5-Aminobenzimidazole → HCID 178446913, compound

HRID 706272

Reaction equation

HRID 706272 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.[CH2:18]([O:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1)[CH2:19][CH2:20][CH2:21][CH3:22].[Si](C#N)(C)(C)C.[N:38]1([C:43](N2C=CN=C2)=[O:44])C=CN=[CH:39]1>>[NH:13]1[C:12]2[CH:16]=[CH:17][C:9]([N:8]3[CH:28]([C:27]4[CH:30]=[CH:31][C:24]([O:23][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:25][CH:26]=4)[CH2:39][NH:38][C:43]3=[O:44])=[CH:10][C:11]=2[N:15]=[CH:14]1

Participants

6

Reactant 5

HCID 136235-AminobenzimidazoleHCID 682631,1'-CarbonyldiimidazoleHCID 79815p-PentoxybenzaldehydeHCID 82115Trimethylsilyl cyanideHCID 84468Trifluoroacetate

Product 1

HCID 178446913HCID 178446913, compound

Procedure

The compound was synthesized as trifluoroacetate salt starting from 5-aminobenzimidazole (0.585 g, 4.4 mmol), 4-pentoxybenzaldehyde (0.755 mL, 4 mmol), TMSCN (0.5 mL, 4 mmol), PdC (10%, 0.02 g), TEA (1.05 mL, 7.4 mmol), di-(imidazol-1-yl)methanone (0.667 g, 4.12 mmol) as described in method 2. The product was purified by means of preparative HPLC.

Workup

  1. customThe product was purified by means of preparative HPLC

Sources & evidence

ORD record
ord-9dc70e34720b4a39bd933560a6186d95
Source dataset
uspto-grants-2015_11
Patent number
US09173885B2

Linked notes

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