5-Aminobenzimidazole → HCID 178517634, compound

HRID 706267Notes

Reaction equation

HRID 706267 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.[CH:18]1([CH:24]=O)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[Si](C#N)(C)(C)C.[N:32]1([C:37](N2C=CN=C2)=[O:38])C=CN=[CH:33]1>>[NH:13]1[C:12]2[CH:16]=[CH:17][C:9]([N:8]3[CH:24]([CH:18]4[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]4)[CH2:33][NH:32][C:37]3=[O:38])=[CH:10][C:11]=2[N:15]=[CH:14]1

Participants

6

Reactant 5

HCID 136235-AminobenzimidazoleHCID 16275CyclohexanecarboxaldehydeHCID 682631,1'-CarbonyldiimidazoleHCID 82115Trimethylsilyl cyanideHCID 84468Trifluoroacetate

Product 1

HCID 178517634HCID 178517634, compound

Procedure

The compound was synthesized as trifluoroacetate salt starting from 5-aminobenzimidazole (0.59 g, 4.4 mmol), cyclohexanecarbaldehyde (0.45 g, 0.485 mL, 4 mmol), TMSCN (0.5 mL, 4 mmol), PdC (10%, 0.05 g). di-(imidazol-1-yl)methanone (0.64 g, 3.92 mmol), as described in method 2. The product was purified via preparative HPLC using a water-acetonitrile gradient with 0.04% trifluoroacetic acid.

Workup

  1. customThe product was purified via preparative HPLC

Sources & evidence

ORD record
ord-9a8d00fb3d44473ead84af90e4be6204
Source dataset
uspto-grants-2015_11
Patent number
US09173885B2

Reaction notes

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