5-Aminobenzimidazole → HCID 51030962, compound

HRID 706280Notes

Reaction equation

HRID 706280 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-d798fb489cba4509ae0ddbb28dc62839
Source dataset
uspto-grants-2015_11
Patent number
US09173885B2

Reaction notes

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