Mavorixafor
货号 B1662892
分子量: 349.5 g/mol
InChI 键: WVLHHLRVNDMIAR-IBGZPJMESA-N
注意: 仅供研究使用。不适用于人类或兽医用途。
Patent
US07354932B2
Procedure details
To a solution of N1-(1-(2-(trimethylsilyl)ethoxymethyl)-1H-Benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine (73 mg, 0.16 mmol) in CH2Cl2 (2 mL) was added trifluoroacetic acid (4 mL) and the resultant solution was stirred at room temperature overnight then concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (10 mL) and water (5 mL) and treated with NaOH (10 M, ˜2 mL) until the aqueous phase was basic (pH 14). The phases were separated and the aqueous phase was extracted with CH2Cl2 (3×10 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by radial chromatography on silica gel (1 mm plate, 15:1:1 CH2Cl2—CH3OH—NH4OH) provided 37 mg of N-(1H-Benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine as a white foam.
Name
N1-(1-(2-(trimethylsilyl)ethoxymethyl)-1H-Benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine
Quantity
73 mg
Type
reactant
Reaction Step One
[Compound]
Name
resultant solution
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Identifiers
|
REACTION_CXSMILES
|
C[Si](C)(C)CCOC[N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[CH2:16][N:17]([CH:23]1[C:32]2[N:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH2:26][CH2:25][CH2:24]1)[CH2:18][CH2:19][CH2:20][CH2:21][NH2:22].FC(F)(F)C(O)=O>C(Cl)Cl>[NH:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[CH2:16][N:17]([CH:23]1[C:32]2[N:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH2:26][CH2:25][CH2:24]1)[CH2:18][CH2:19][CH2:20][CH2:21][NH2:22]
|
Inputs
Step One
|
Name
|
N1-(1-(2-(trimethylsilyl)ethoxymethyl)-1H-Benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine
|
|
Quantity
|
73 mg
|
|
Type
|
reactant
|
|
Smiles
|
C[Si](CCOCN1C(=NC2=C1C=CC=C2)CN(CCCCN)C2CCCC=1C=CC=NC21)(C)C
|
|
Name
|
|
|
Quantity
|
4 mL
|
|
Type
|
reactant
|
|
Smiles
|
FC(C(=O)O)(F)F
|
|
Name
|
|
|
Quantity
|
2 mL
|
|
Type
|
solvent
|
|
Smiles
|
C(Cl)Cl
|
Step Two
[Compound]
|
Name
|
resultant solution
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
|
Conditions
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
then concentrated under reduced pressure
|
DISSOLUTION
|
Type
|
DISSOLUTION
|
|
Details
|
The residue was dissolved in CH2Cl2 (10 mL)
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
water (5 mL) and treated with NaOH (10 M, ˜2 mL) until the aqueous phase
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The phases were separated
|
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
the aqueous phase was extracted with CH2Cl2 (3×10 mL)
|
DRY_WITH_MATERIAL
|
Type
|
DRY_WITH_MATERIAL
|
|
Details
|
The combined organic extracts were dried (Na2SO4)
|
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
concentrated
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
Purification of the crude material by radial chromatography on silica gel (1 mm plate, 15:1:1 CH2Cl2—CH3OH—NH4OH)
|
Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
N1C(=NC2=C1C=CC=C2)CN(CCCCN)C2CCCC=1C=CC=NC21
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 37 mg | |
| YIELD: CALCULATEDPERCENTYIELD | 66.2% |
Source
|
Source
|
Open Reaction Database (ORD) |
|
Description
|
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks. |
Patent
US07354932B2
Procedure details
To a solution of N1-(1-(2-(trimethylsilyl)ethoxymethyl)-1H-Benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine (73 mg, 0.16 mmol) in CH2Cl2 (2 mL) was added trifluoroacetic acid (4 mL) and the resultant solution was stirred at room temperature overnight then concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (10 mL) and water (5 mL) and treated with NaOH (10 M, ˜2 mL) until the aqueous phase was basic (pH 14). The phases were separated and the aqueous phase was extracted with CH2Cl2 (3×10 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by radial chromatography on silica gel (1 mm plate, 15:1:1 CH2Cl2—CH3OH—NH4OH) provided 37 mg of N-(1H-Benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine as a white foam.
Name
N1-(1-(2-(trimethylsilyl)ethoxymethyl)-1H-Benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine
Quantity
73 mg
Type
reactant
Reaction Step One
[Compound]
Name
resultant solution
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Identifiers
|
REACTION_CXSMILES
|
C[Si](C)(C)CCOC[N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[CH2:16][N:17]([CH:23]1[C:32]2[N:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH2:26][CH2:25][CH2:24]1)[CH2:18][CH2:19][CH2:20][CH2:21][NH2:22].FC(F)(F)C(O)=O>C(Cl)Cl>[NH:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[CH2:16][N:17]([CH:23]1[C:32]2[N:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH2:26][CH2:25][CH2:24]1)[CH2:18][CH2:19][CH2:20][CH2:21][NH2:22]
|
Inputs
Step One
|
Name
|
N1-(1-(2-(trimethylsilyl)ethoxymethyl)-1H-Benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine
|
|
Quantity
|
73 mg
|
|
Type
|
reactant
|
|
Smiles
|
C[Si](CCOCN1C(=NC2=C1C=CC=C2)CN(CCCCN)C2CCCC=1C=CC=NC21)(C)C
|
|
Name
|
|
|
Quantity
|
4 mL
|
|
Type
|
reactant
|
|
Smiles
|
FC(C(=O)O)(F)F
|
|
Name
|
|
|
Quantity
|
2 mL
|
|
Type
|
solvent
|
|
Smiles
|
C(Cl)Cl
|
Step Two
[Compound]
|
Name
|
resultant solution
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
|
Conditions
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
then concentrated under reduced pressure
|
DISSOLUTION
|
Type
|
DISSOLUTION
|
|
Details
|
The residue was dissolved in CH2Cl2 (10 mL)
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
water (5 mL) and treated with NaOH (10 M, ˜2 mL) until the aqueous phase
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The phases were separated
|
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
the aqueous phase was extracted with CH2Cl2 (3×10 mL)
|
DRY_WITH_MATERIAL
|
Type
|
DRY_WITH_MATERIAL
|
|
Details
|
The combined organic extracts were dried (Na2SO4)
|
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
concentrated
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
Purification of the crude material by radial chromatography on silica gel (1 mm plate, 15:1:1 CH2Cl2—CH3OH—NH4OH)
|
Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
N1C(=NC2=C1C=CC=C2)CN(CCCCN)C2CCCC=1C=CC=NC21
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 37 mg | |
| YIELD: CALCULATEDPERCENTYIELD | 66.2% |
Source
|
Source
|
Open Reaction Database (ORD) |
|
Description
|
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks. |
