2,6-Dichlorobenzaldehyde → HCID 178517681, compound

HRID 452083Notes

Reaction equation

HRID 452083 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.[Cl:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:20]=1[CH:21]=O.[Si](C#N)(C)(C)C.[N:34]1([C:39](N2C=CN=C2)=[O:40])C=CN=[CH:35]1>>[NH:13]1[C:12]2[CH:16]=[CH:17][C:9]([N:8]3[CH:21]([C:20]4[C:19]([Cl:18])=[CH:26][CH:25]=[CH:24][C:23]=4[Cl:27])[CH2:35][NH:34][C:39]3=[O:40])=[CH:10][C:11]=2[N:15]=[CH:14]1

Participants

6

Reactant 5

HCID 67372,6-DichlorobenzaldehydeHCID 136235-AminobenzimidazoleHCID 682631,1'-CarbonyldiimidazoleHCID 82115Trimethylsilyl cyanideHCID 84468Trifluoroacetate

Product 1

HCID 178517681HCID 178517681, compound

Procedure

The compound was synthesized as trifluoroacetate salt starting from 5-aminobenzimidazole (0.585 g, 4.4 mmol), 2,6-dichloro-benzaldehyde (0.7 g, 4 mmol), TMSCN (0.5 mL, 4 mmol), PdC (10%, 0.02 g), TEA (0.4 mL, 2.8 mmol), di-(imidazol-1-yl)methanone (0.253 g, 1.56 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-58ca1a7694404dd2b1fe4c16e14f6d54
Source dataset
uspto-grants-2013_07
Patent number
US08486940B2

Reaction notes

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