5-Aminobenzimidazole → HCID 178450103, compound

HRID 706271Notes

Reaction equation

HRID 706271 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:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1)[CH2:19][CH2:20][CH3:21].[Si](C#N)(C)(C)C.[N:37]1([C:42](N2C=CN=C2)=[O:43])C=CN=[CH:38]1>>[NH:13]1[C:12]2[CH:16]=[CH:17][C:9]([N:8]3[CH:27]([C:26]4[CH:29]=[CH:30][C:23]([O:22][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:24][CH:25]=4)[CH2:38][NH:37][C:42]3=[O:43])=[CH:10][C:11]=2[N:15]=[CH:14]1

Participants

6

Reactant 5

HCID 136235-AminobenzimidazoleHCID 682631,1'-CarbonyldiimidazoleHCID 798134-ButoxybenzaldehydeHCID 82115Trimethylsilyl cyanideHCID 84468Trifluoroacetate

Product 1

HCID 178450103HCID 178450103, compound

Procedure

The compound was synthesized as trifluoroacetate salt starting from 5-aminobenzimidazole (0.585 g, 4.4 mmol), 4-butoxybenzaldehyde (0.691 mL, 4 mmol), TMSCN (0.5 mL, 4 mmol), PdC (10%, 0.02 g), TEA (1.03 mL, 7.4 mmol), di-(imidazol-1-yl)methanone (0.658, 4.06 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-16cf0e95819544a9ab4dd93e39ba0095
Source dataset
uspto-grants-2015_11
Patent number
US09173885B2

Reaction notes

Loading…