5-Aminobenzimidazole → HCID 178458236, compound

HRID 706273Notes

Reaction equation

HRID 706273 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]([O:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1)([CH3:20])[CH3:19].[Si](C#N)(C)(C)C.[N:36]1([C:41](N2C=CN=C2)=[O:42])C=CN=[CH:37]1>>[NH:13]1[C:12]2[CH:16]=[CH:17][C:9]([N:8]3[CH:26]([C:25]4[CH:28]=[CH:29][C:22]([O:21][CH:18]([CH3:20])[CH3:19])=[CH:23][CH:24]=4)[CH2:37][NH:36][C:41]3=[O:42])=[CH:10][C:11]=2[N:15]=[CH:14]1

Participants

6

Reactant 5

HCID 136235-AminobenzimidazoleHCID 682631,1'-CarbonyldiimidazoleHCID 82115Trimethylsilyl cyanideHCID 84468TrifluoroacetateHCID 2500774-Isopropoxybenzaldehyde

Product 1

HCID 178458236HCID 178458236, compound

Procedure

The compound was synthesized as trifluoroacetate salt starting from 5-aminobenzimidazole (0.585 g, 4.4 mmol), 4-isopropoxybenzaldehyde (0.657 g, 4 mmol), TMSCN (0.5 mL, 4 mmol), PdC (10%, 0.02 g), TEA (0.889 mL, 6.38 mmol), di-(imidazol-1-yl)methanone (0.564, 3.48 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-792025af06d54581909398e44f1fa72f
Source dataset
uspto-grants-2015_11
Patent number
US09173885B2

Reaction notes

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