1,2-Dichloroethane → HCID 178490491, compound

HRID 1012074Notes

Reaction equation

HRID 1012074 reaction equation
[F:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[C:14]1[C:22]1[C:26]([NH2:27])=[CH:25][NH:24][N:23]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[NH:15]1[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N:13]=[C:14]1[C:22]1[C:26]([NH:27][C:4](=[O:6])[C:3]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH3:12])[C:2]=2[F:1])=[CH:25][NH:24][N:23]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 33906792-Fluoro-3-methoxybenzoic acidHCID 178508052HCID 178508052, compound

Product 1

HCID 178490491HCID 178490491, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-fluoro-3-methoxybenzoic acid (47 mg, 0.28 mmol), 3-(1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine (50 mg, 0.25 mmol), EDC (58 mg, 0.30 mmol) and HOBt (41 mg, 0.30 mmol) in DMF (1.5 ml) was stirred at ambient temperature for 20 h. The reaction mixture was poured into water (30 ml) and the resultant solid collected by filtration and purified by re-crystallisation from MeOH/petrol to yield N-[3-(1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-2-fluoro-3-methoxy-benzamide (7 mg, 8%) as a gray solid. (LC/MS: Rt 3.63, [M+H]+ 352.00).

Workup

  1. filtrationthe resultant solid collected by filtration
  2. custompurified by re-crystallisation from MeOH/petrol

Sources & evidence

ORD record
ord-0b278389dc25448eb0225934298eaab1
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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