1,2-Dichloroethane → HCID 178522416, compound

HRID 1012084Notes

Reaction equation

HRID 1012084 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([OH:13])=O)[CH:4]=[CH:3][CH:2]=1.[NH:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[C:23]1[C:27]([NH2:28])=[CH:26][NH:25][N:24]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[NH:16]1[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:14]=[C:15]1[C:23]1[C:27]([NH:28][C:11]([C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[C:10]=2[N:1]=[CH:2][CH:3]=[CH:4]3)=[O:13])=[CH:26][NH:25][N:24]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 665828-Quinolinecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 178508052HCID 178508052, compound

Product 1

HCID 178522416HCID 178522416, compoundYield 6.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of quinoline-8-carboxylic acid (104 mg, 0.60 mmol), 3-(1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine (100 mg, 0.50 mmol), EDC (116 mg, 0.60 mmol) and HOBt (81 mg, 0.60 mmol) was stirred at room temperature in DMF (1.5 ml) for 20 h. The reaction mixture was purified by preparative LC/MS to give quinoline-8-carboxylic acid [3-(1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-amide (11 mg, 6%) as a brown solid. (LC/MS: Rt 3.85, [M+H]+ 355.11).

Workup

  1. customThe reaction mixture was purified by preparative LC/MS

Sources & evidence

ORD record
ord-151c8476c6b74b4f828fc2412acbab00
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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