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 (1-tert-butoxycarbonyl-1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (0.169 g, 0.451 mmol) in CH3CN (5 mL) was added N,N-diisopropylethylamine (0.25 mL, 1.44 mmol) followed by 4-bromobutyronitrile (0.10 mL, 1.01 mmol). The resultant mixture was heated to 80° C. for 5 d then cooled to room temperature. The mixture was concentrated and the residue was partitioned between CH2Cl2 (20 mL) and brine (10 mL). 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 column chromatography on silica gel (30:1:1 CH2Cl2—CH3OH—NH4OH) provided 108 mg (54%) of a yellow foam.
Name
(1-tert-butoxycarbonyl-1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine
Quantity
0.169 g
Type
reactant
Reaction Step One
[Compound]
Name
resultant mixture
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Name
Yield
54%
Identifiers
|
REACTION_CXSMILES
|
C(OC([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:17][NH:18][CH:19]1[C:28]2[N:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:22][CH2:21][CH2:20]1)=O)(C)(C)C.C(N(CC)C(C)C)(C)C.Br[CH2:39][CH2:40][CH2:41][C:42]#[N:43]>CC#N>[NH:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:8]=[C:9]1[CH2:17][N:18]([CH:19]1[C:28]2[N:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:22][CH2:21][CH2:20]1)[CH2:39][CH2:40][CH2:41][CH2:42][NH2:43]
|
Inputs
Step One
|
Name
|
(1-tert-butoxycarbonyl-1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine
|
|
Quantity
|
0.169 g
|
|
Type
|
reactant
|
|
Smiles
|
C(C)(C)(C)OC(=O)N1C(=NC2=C1C=CC=C2)CNC2CCCC=1C=CC=NC21
|
|
Name
|
|
|
Quantity
|
0.25 mL
|
|
Type
|
reactant
|
|
Smiles
|
C(C)(C)N(C(C)C)CC
|
|
Name
|
|
|
Quantity
|
5 mL
|
|
Type
|
solvent
|
|
Smiles
|
CC#N
|
Step Two
|
Name
|
|
|
Quantity
|
0.1 mL
|
|
Type
|
reactant
|
|
Smiles
|
BrCCCC#N
|
Step Three
[Compound]
|
Name
|
resultant mixture
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
|
Conditions
Temperature
|
Control Type
|
AMBIENT
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
The mixture was concentrated
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
the residue was partitioned between CH2Cl2 (20 mL) and brine (10 mL)
|
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 column chromatography on silica gel (30:1:1 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 | 108 mg | |
| YIELD: PERCENTYIELD | 54% | |
| YIELD: CALCULATEDPERCENTYIELD | 68.5% |
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 (1-tert-butoxycarbonyl-1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (0.169 g, 0.451 mmol) in CH3CN (5 mL) was added N,N-diisopropylethylamine (0.25 mL, 1.44 mmol) followed by 4-bromobutyronitrile (0.10 mL, 1.01 mmol). The resultant mixture was heated to 80° C. for 5 d then cooled to room temperature. The mixture was concentrated and the residue was partitioned between CH2Cl2 (20 mL) and brine (10 mL). 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 column chromatography on silica gel (30:1:1 CH2Cl2—CH3OH—NH4OH) provided 108 mg (54%) of a yellow foam.
Name
(1-tert-butoxycarbonyl-1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine
Quantity
0.169 g
Type
reactant
Reaction Step One
[Compound]
Name
resultant mixture
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Name
Yield
54%
Identifiers
|
REACTION_CXSMILES
|
C(OC([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:17][NH:18][CH:19]1[C:28]2[N:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:22][CH2:21][CH2:20]1)=O)(C)(C)C.C(N(CC)C(C)C)(C)C.Br[CH2:39][CH2:40][CH2:41][C:42]#[N:43]>CC#N>[NH:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:8]=[C:9]1[CH2:17][N:18]([CH:19]1[C:28]2[N:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:22][CH2:21][CH2:20]1)[CH2:39][CH2:40][CH2:41][CH2:42][NH2:43]
|
Inputs
Step One
|
Name
|
(1-tert-butoxycarbonyl-1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine
|
|
Quantity
|
0.169 g
|
|
Type
|
reactant
|
|
Smiles
|
C(C)(C)(C)OC(=O)N1C(=NC2=C1C=CC=C2)CNC2CCCC=1C=CC=NC21
|
|
Name
|
|
|
Quantity
|
0.25 mL
|
|
Type
|
reactant
|
|
Smiles
|
C(C)(C)N(C(C)C)CC
|
|
Name
|
|
|
Quantity
|
5 mL
|
|
Type
|
solvent
|
|
Smiles
|
CC#N
|
Step Two
|
Name
|
|
|
Quantity
|
0.1 mL
|
|
Type
|
reactant
|
|
Smiles
|
BrCCCC#N
|
Step Three
[Compound]
|
Name
|
resultant mixture
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
|
Conditions
Temperature
|
Control Type
|
AMBIENT
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
The mixture was concentrated
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
the residue was partitioned between CH2Cl2 (20 mL) and brine (10 mL)
|
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 column chromatography on silica gel (30:1:1 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 | 108 mg | |
| YIELD: PERCENTYIELD | 54% | |
| YIELD: CALCULATEDPERCENTYIELD | 68.5% |
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. |
