5-Aminobenzimidazole → HCID 178446913, compound

HRID 452063

Reaction equation

HRID 452063 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-fef5e30579e3444089a7a1150f520b34
Source dataset
uspto-grants-2013_07
Patent number
US08486940B2

Linked notes

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