5-Aminobenzimidazole → HCID 178517648, compound

HRID 452074Notes

Reaction equation

HRID 452074 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:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=O.[Si](C#N)(C)(C)C.[N:33]1([C:38](N2C=CN=C2)=[O:39])C=CN=[CH:34]1>>[NH:13]1[C:12]2[CH:16]=[CH:17][C:9]([N:8]3[CH:22]([C:21]4[CH:24]=[CH:25][CH:26]=[C:19]([F:18])[CH:20]=4)[CH2:34][NH:33][C:38]3=[O:39])=[CH:10][C:11]=2[N:15]=[CH:14]1

Participants

6

Reactant 5

HCID 136235-AminobenzimidazoleHCID 680093-FluorobenzaldehydeHCID 682631,1'-CarbonyldiimidazoleHCID 82115Trimethylsilyl cyanideHCID 84468Trifluoroacetate

Product 1

HCID 178517648HCID 178517648, compound

Procedure

The compound was synthesized as trifluoroacetate salt starting from 5-aminobenzimidazole (0.585 g, 4.4 mmol), 3-fluorobenzaldehyde (0.496 g, 4 mmol), TMSCN (0.5 mL, 4 mmol), PdC (10%, 0.02 g), TEA (0.979 mL, 7.02 mmol), di-(imidazol-1-yl)methanone (0.621, 3.83 mmol) as described in method 2.

Sources & evidence

ORD record
ord-aad46d7dd34b45a0aebed5d00a6230cb
Source dataset
uspto-grants-2013_07
Patent number
US08486940B2

Reaction notes

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