1H-Benzimidazole-6-carboxamide → 1-(6-{[1-(3-fluorophenyl)ethyl]amino}pyrazin-2-yl)-1H-benzimidazole-6-carboxamide

HRID 16137Notes

Reaction equation

HRID 16137 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[CH3:10])[CH:5]=[N:4][CH:3]=1.[NH:18]1[C:22]2[CH:23]=[CH:24][C:25]([C:27]([NH2:29])=[O:28])=[CH:26][C:21]=2[N:20]=[CH:19]1>>[F:17][C:13]1[CH:12]=[C:11]([CH:9]([NH:8][C:6]2[N:7]=[C:2]([N:20]3[C:21]4[CH:26]=[C:25]([C:27]([NH2:29])=[O:28])[CH:24]=[CH:23][C:22]=4[N:18]=[CH:19]3)[CH:3]=[N:4][CH:5]=2)[CH3:10])[CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 154216421H-Benzimidazole-6-carboxamideHCID 588699296-chloro-N-[1-(3-fluorophenyl)ethyl]pyrazin-2-amine

Product 1

HCID 112573781-(6-{[1-(3-fluorophenyl)ethyl]amino}pyrazin-2-yl)-1H-benzimidazole-6-carboxamideYield 21.3%

Procedure

In an analogous fashion, to Example 3, 6-chloro-N-[1-(3-fluorophenyl)ethyl]pyrazin-2-amine (025 g, 1 mmol) was reacted with 1H-benzimidazole-5-carboxamide (0.2 g, 1.2 mmol) to afford the product as a mixture of isomers. These were separated by chromatography using dichloromethane-methanol (98:2-92:8) as eluant to afford from the less polar fractions 1-(6-{[1-(3-fluorophenyl)ethyl]amino}pyrazin-2-yl)-1H-benzimidazole-6-carboxamide (80 mg).

Workup

  1. customto afford the product
  2. additionas a mixture of isomers
  3. customThese were separated by chromatography

Sources & evidence

ORD record
ord-cd9232f1c68d4987a4529275ab78bf29
Source dataset
uspto-grants-2010_06
Patent number
US07737143B2

Reaction notes

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