Phosphorus oxychloride → 1-(6-[[1-(3-fluorophenyl)ethyl]amino]pyrazin-2-yl)-1H-benzimidazole-6-carbonitrile

HRID 16138Notes

Reaction equation

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

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

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

Product 1

HCID 114397611-(6-[[1-(3-fluorophenyl)ethyl]amino]pyrazin-2-yl)-1H-benzimidazole-6-carbonitrileYield 80%

Procedure

In an analogous procedure to that reported in Example 4, 1-(6-{[1-(3-fluorophenyl)ethyl]amino}pyrazin-2-yl)-1H-benzimidazole-6-carboxamide (83 mg 0.21 mmol) was reacted with phosphorus oxychloride to afford the product as a pale yellow solid (60 mg, 80%).

Sources & evidence

ORD record: ord-0decf2fbbf764e13806159996ca3156c
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737143B2

Reaction notes

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