![molecular formula C15H10BrClFN3O2 B1317276 5-((4-Bromo-2-chlorophenyl)amino)-4-fluoro-1-methyl-1H-benzo[d]imidazole-6-carboxylic acid CAS No. 606144-04-1](/img/structure/B1317276.png)
5-((4-Bromo-2-chlorophenyl)amino)-4-fluoro-1-methyl-1H-benzo[d]imidazole-6-carboxylic acid
Katalognummer B1317276
Molekulargewicht: 398.61 g/mol
InChI-Schlüssel: XAAPQRFIXGDKPZ-UHFFFAOYSA-N
Achtung: Nur für Forschungszwecke. Nicht für den menschlichen oder tierärztlichen Gebrauch.
Patent
US07425637B2
Procedure details
6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid 10c (2.00 g, 5.0 mmol), O-(2-vinyloxy-ethyl)-hydroxylamine (0.776 g, 7.5 mmol), HOBt (0.88 g, 6.5 mmol), triethylamine (1.61 mL, 2.3 mmol) and EDCI (1.3 g, 6.5 mmol) are dissolved in dimethylformamide (52 mL) and stirred at room temperature for 48 hours. The reaction mixture is diluted with ethyl acetate, washed with water (3×), saturated potassium carbonate (2×), saturated ammonium chloride (2×), brine, dried (Na2SO4) and concentrated under reduced pressure to an off-white solid. Trituration of the solid with diethyl ether provides 2.18 g (90%) desired product as an off-white solid. MS ESI (+) m/z 483, 485 (M+Br pattern) detected.
Quantity
2 g
Type
reactant
Reaction Step One
Name
Yield
90%
Identifiers
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REACTION_CXSMILES
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[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([C:20]([OH:22])=O)=[CH:11][C:12]3[N:16]([CH3:17])[CH:15]=[N:14][C:13]=3[C:18]=2[F:19])=[C:4]([Cl:23])[CH:3]=1.[CH:24]([O:26][CH2:27][CH2:28][O:29][NH2:30])=[CH2:25].C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.CCN=C=NCCCN(C)C>CN(C)C=O.C(OCC)(=O)C>[CH:24]([O:26][CH2:27][CH2:28][O:29][NH:30][C:20]([C:10]1[C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[Cl:23])=[C:18]([F:19])[C:13]2[N:14]=[CH:15][N:16]([CH3:17])[C:12]=2[CH:11]=1)=[O:22])=[CH2:25]
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Inputs
Step One
|
Name
|
|
|
Quantity
|
2 g
|
|
Type
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reactant
|
|
Smiles
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BrC1=CC(=C(C=C1)NC=1C(=CC2=C(N=CN2C)C1F)C(=O)O)Cl
|
|
Name
|
|
|
Quantity
|
0.776 g
|
|
Type
|
reactant
|
|
Smiles
|
C(=C)OCCON
|
|
Name
|
|
|
Quantity
|
0.88 g
|
|
Type
|
reactant
|
|
Smiles
|
C=1C=CC2=C(C1)N=NN2O
|
|
Name
|
|
|
Quantity
|
1.61 mL
|
|
Type
|
reactant
|
|
Smiles
|
C(C)N(CC)CC
|
|
Name
|
|
|
Quantity
|
1.3 g
|
|
Type
|
reactant
|
|
Smiles
|
CCN=C=NCCCN(C)C
|
|
Name
|
|
|
Quantity
|
52 mL
|
|
Type
|
solvent
|
|
Smiles
|
CN(C=O)C
|
Step Two
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
C(C)(=O)OCC
|
Conditions
Temperature
|
Control Type
|
AMBIENT
|
Stirring
|
Type
|
CUSTOM
|
|
Details
|
stirred at room temperature for 48 hours
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
WASH
|
Type
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WASH
|
|
Details
|
washed with water (3×), saturated potassium carbonate (2×), saturated ammonium chloride (2×), brine
|
DRY_WITH_MATERIAL
|
Type
|
DRY_WITH_MATERIAL
|
|
Details
|
dried (Na2SO4)
|
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
concentrated under reduced pressure to an off-white solid
|
Outcomes
Product
Details
Reaction Time |
48 h |
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
C(=C)OCCONC(=O)C1=CC2=C(N=CN2C)C(=C1NC1=C(C=C(C=C1)Br)Cl)F
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 2.18 g | |
| YIELD: PERCENTYIELD | 90% | |
| YIELD: CALCULATEDPERCENTYIELD | 90.1% |
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. |
