5-Aminobenzimidazole → HCID 178517612, compound

HRID 706277Notes

Reaction equation

HRID 706277 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.[F:11][C:12]1([F:23])[O:16][C:15]2[CH:17]=[CH:18][C:19]([CH:21]=O)=[CH:20][C:14]=2[O:13]1.[Si](C#N)(C)(C)C.[N:30]1([C:35](N2C=CN=C2)=[O:36])C=CN=[CH:31]1>>[NH:6]1[C:5]2[CH:9]=[CH:10][C:2]([N:1]3[CH:21]([C:19]4[CH:18]=[CH:17][C:15]5[O:16][C:12]([F:23])([F:11])[O:13][C:14]=5[CH:20]=4)[CH2:31][NH:30][C:35]3=[O:36])=[CH:3][C:4]=2[N:8]=[CH:7]1

Participants

5

Reactant 4

HCID 136235-AminobenzimidazoleHCID 682631,1'-CarbonyldiimidazoleHCID 82115Trimethylsilyl cyanideHCID 27369732,2-Difluoro-5-formylbenzodioxole

Product 1

HCID 178517612HCID 178517612, compound

Procedure

The compound was synthesized starting from 5-aminobenzimidazole (0.585 g, 4.4 mmol), 2,2-difluorobenzo[d][1,3]dioxole-5-carbaldehyde (0.744 g, 4 mmol), TMSCN (0.5 mL, 4 mmol), PdC (10%, 0.02 g), TEA (0.81 mL, 5.81 mmol), di-(imidazol-1-yl)methanone (0.514 g, 3.17 mmol) as described in method 2. The product was purified by means of FPLC.

Workup

  1. customThe compound was synthesized
  2. customThe product was purified by means of FPLC

Sources & evidence

ORD record
ord-5c06ece1e4d44e4393a5211b4dbdf283
Source dataset
uspto-grants-2015_11
Patent number
US09173885B2

Reaction notes

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