5-Aminobenzimidazole → HCID 178517612, compound

HRID 452068Notes

Reaction equation

HRID 452068 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-d7cd3b0f3dc045599331c5d10d3c1123
Source dataset
uspto-grants-2013_07
Patent number
US08486940B2

Reaction notes

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