5-Aminobenzimidazole → HCID 178517683, compound

HRID 706284Notes

Reaction equation

HRID 706284 reaction equation
FC(F)(F)C([O-])=O.[NH2:8][C:9]1[CH:17]=[CH:16][C:12]2[N:13]=[CH:14][NH:15][C:11]=2[CH:10]=1.[F:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:20]=1[CH:21]=O.[Si](C#N)(C)(C)C.[N:34]1([C:39](N2C=CN=C2)=[O:40])C=CN=[CH:35]1>>[NH:13]1[C:12]2[CH:16]=[CH:17][C:9]([N:8]3[CH:21]([C:20]4[C:19]([F:18])=[CH:26][CH:25]=[CH:24][C:23]=4[F:27])[CH2:35][NH:34][C:39]3=[O:40])=[CH:10][C:11]=2[N:15]=[CH:14]1

Participants

6

Reactant 5

HCID 136235-AminobenzimidazoleHCID 682631,1'-CarbonyldiimidazoleHCID 82115Trimethylsilyl cyanideHCID 84468TrifluoroacetateHCID 1362842,6-Difluorobenzaldehyde

Product 1

HCID 178517683HCID 178517683, compound

Procedure

The compound was synthesized as trifluoroacetate salt starting from 5-aminobenzimidazole (0.585 g, 4.4 mmol), 2,6-difluorobenzaldehyde (0.431 mL, 4 mmol), TMSCN (0.5 mL, 4 mmol), PdC (10%, 0.02 g), TEA (1.15 mL, 8.22 mmol), di-(imidazol-1-yl)methanone (0.730, 4.5 mmol) as described in method 2.

Sources & evidence

ORD record
ord-4c84a7ee78b94b66a6e65f133b262a78
Source dataset
uspto-grants-2015_11
Patent number
US09173885B2

Reaction notes

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