3-Chlorobenzaldehyde → HCID 178517646, compound

HRID 706291Notes

Reaction equation

HRID 706291 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:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=O.[Si](C#N)(C)(C)C.[N:33]1([C:38](N2C=CN=C2)=[O:39])C=CN=[CH:34]1>>[NH:13]1[C:12]2[CH:16]=[CH:17][C:9]([N:8]3[CH:22]([C:21]4[CH:24]=[CH:25][CH:26]=[C:19]([Cl:18])[CH:20]=4)[CH2:34][NH:33][C:38]3=[O:39])=[CH:10][C:11]=2[N:15]=[CH:14]1

Participants

6

Reactant 5

HCID 114773-ChlorobenzaldehydeHCID 136235-AminobenzimidazoleHCID 682631,1'-CarbonyldiimidazoleHCID 82115Trimethylsilyl cyanideHCID 84468Trifluoroacetate

Product 1

HCID 178517646HCID 178517646, compound

Procedure

The compound was synthesized as trifluoroacetate salt starting from 5-aminobenzimidazole (0.293 g, 2.2 mmol), 3-chloro benzaldehyde (0.227 mL, 2 mmol), TMSCN (0.25 mL, 2 mmol), PdC (10%, 0.01 g), TEA (0.613 mL, 4.4 mmol), di-(imidazol-1-yl)methanone (0.389 g, 2.4 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-de3a5e03cab64974abf5f691c45b917b
Source dataset
uspto-grants-2015_11
Patent number
US09173885B2

Reaction notes

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