1,2-Dichloroethane → HCID 178481037, compound

HRID 1012080Notes

Reaction equation

HRID 1012080 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:3]=1[C:4]([NH:6][C:7]1[C:8]([C:12]2[NH:16][C:15]3[CH:17]=[CH:18][CH:19]=[C:20]([C:21](O)=[O:22])[C:14]=3[N:13]=2)=[N:9][NH:10][CH:11]=1)=[O:5].[CH3:29][N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:3]=1[C:4]([NH:6][C:7]1[C:8]([C:12]2[NH:16][C:15]3[CH:17]=[CH:18][CH:19]=[C:20]([C:21]([N:33]4[CH2:34][CH2:35][N:30]([CH3:29])[CH2:31][CH2:32]4)=[O:22])[C:14]=3[N:13]=2)=[N:9][NH:10][CH:11]=1)=[O:5]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 178522445HCID 178522445, compound

Product 1

HCID 178481037HCID 178481037, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[4-(2,6-difluoro-benzoylamino)-1H-pyrazol-3-yl]-1H-benzimidazole-4-carboxylic acid (50 mg, 0.13 mmol), N-methylpiperazine (20 μl, 0.18 mmol), EDC (30 mg, 0.15 mmol) and HOBt (22 mg, 0.15 mmol) in DMF (5 ml) was stirred at ambient temperature for 18 h. The mixture was reduced in vacuo and the residue purified by flash column chromatography [SiO2, CH2Cl2/MeOH (95:5, 90:10)] to give 2,6-difluoro-N-{3-[4-(4-methyl-piperazine-1-carbonyl)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl}-benzamide (14 mg) as a cream solid. (LC/MS: Rt 2.21, [M+H]+ 466).

Workup

  1. customthe residue purified by flash column chromatography [SiO2, CH2Cl2/MeOH (95:5, 90:10)]

Sources & evidence

ORD record
ord-f59e488ad7ac41e4826e69c193b14d27
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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