5-Aminobenzimidazole → HCID 51030962, compound

HRID 452071

Reaction equation

HRID 452071 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]2[N:6]=[CH:7][NH:8][C:4]=2[CH:3]=1.[O:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][O:19][C:20]2[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=2)[CH2:13][CH2:12]1.[Si](C#N)(C)(C)C.[N:34]1([C:39](N2C=CN=C2)=[O:40])C=CN=[CH:35]1>>[O:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][O:19][C:20]2[CH:27]=[CH:26][C:23]([CH:24]3[N:1]([C:2]4[CH:10]=[CH:9][C:5]5[N:6]=[CH:7][NH:8][C:4]=5[CH:3]=4)[C:39](=[O:40])[NH:34][CH2:35]3)=[CH:22][CH:21]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 4

HCID 136235-AminobenzimidazoleHCID 682631,1'-CarbonyldiimidazoleHCID 82115Trimethylsilyl cyanideHCID 37199024-(2-Morpholinoethoxy)benzaldehyde

Product 1

HCID 51030962HCID 51030962, compound

Procedure

The compound was synthesized as ditrifluoroacetate salt starting from 5-aminobenzimidazole (0.585 g, 4.4 mmol), 4-(2-morpholinoethoxy)benzaldehyde (0.941 g, 4 mmol), TMSCN (0.5 mL, 4 mmol), PdC (10%, 0.02 g), TEA (1.34 mL, 9.6 mmol), di-(imidazol-1-yl)methanone (0.582 g, 3.6 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-a09b34d2006140fb960c4f057a2d045f
Source dataset
uspto-grants-2013_07
Patent number
US08486940B2

Linked notes

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