2,6-Dichlorobenzaldehyde → HCID 178517681, compound

HRID 706292Notes

Reaction equation

HRID 706292 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-321caa0a0420425d8b7bc91418229f7b
Source dataset
uspto-grants-2015_11
Patent number
US09173885B2

Reaction notes

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