5-Aminobenzimidazole → HCID 178487637, compound

HRID 706274Notes

Reaction equation

HRID 706274 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.[CH3:18][O:19][C:20]1[C:25]2[O:26][CH2:27][O:28][C:24]=2[CH:23]=[C:22]([CH:29]=O)[CH:21]=1.[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:29]([C:22]4[CH:21]=[C:20]([O:19][CH3:18])[C:25]5[O:26][CH2:27][O:28][C:24]=5[CH:23]=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 220161,3-Benzodioxole-5-carboxaldehyde, 7-methoxy-HCID 682631,1'-CarbonyldiimidazoleHCID 82115Trimethylsilyl cyanideHCID 84468Trifluoroacetate

Product 1

HCID 178487637HCID 178487637, compound

Procedure

The compound was synthesized as trifluoroacetate salt starting from 5-aminobenzimidazole (0.585 g, 4.4 mmol), 7-methoxybenzo[d][1,3]dioxole-5-carbaldehyde (0.721 g, 4 mmol), TMSCN (0.5 mL, 4 mmol), PdC (10%, 0.02 g), TEA (0.521 mL, 3.74 mmol), di-(imidazol-1-yl)methanone (0.331 g, 2.04 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-fb9324cce08e40c3b6aceb3d774131e6
Source dataset
uspto-grants-2015_11
Patent number
US09173885B2

Reaction notes

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