2-Thiophenecarbonyl chloride → HCID 10166146, compound

HRID 2416922Notes

Reaction equation

HRID 2416922 reaction equation
[CH:1]1([N:7]([CH3:24])[C:8]([C:10]2[CH:23]=[CH:22][C:13]3[N:14]([CH2:18][CH2:19][CH2:20][OH:21])[C:15]([NH2:17])=[N:16][C:12]=3[CH:11]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[S:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[C:30](Cl)=[O:31]>N1C=CC=CC=1>[CH:1]1([N:7]([CH3:24])[C:8]([C:10]2[CH:23]=[CH:22][C:13]3[N:14]([CH2:18][CH2:19][CH2:20][O:21][C:30]([C:26]4[S:25][CH:29]=[CH:28][CH:27]=4)=[O:31])[C:15]([NH:17][C:30]([C:26]4[S:25][CH:29]=[CH:28][CH:27]=4)=[O:31])=[N:16][C:12]=3[CH:11]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 789282-Thiophenecarbonyl chlorideHCID 59083107HCID 59083107, compound

Product 1

HCID 10166146HCID 10166146, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of the above amino benzimidazole (0.7 g, 2.1 mmol) in pyridine (10 mL) was added 2-thiophenecarbonyl chloride (0.68 mL, 6.4 mmol). The reaction was complete in 6 h. The pyridine was evaporated and the resulting orange solid was purified by flash chromatography with 1% MeOH/dichloromethane to give thiophene-2-carboxylic acid 3-{5-(cyclohexyl-methyl-carbamoyl)-2-[(thiophene-2-carbonyl)-amino]-benzoimidazol-1-yl}-propyl ester (0.50 g, 43%), m.p. 92-94° C.

Workup

  1. customThe pyridine was evaporated
  2. customthe resulting orange solid was purified by flash chromatography with 1% MeOH/dichloromethane

Sources & evidence

ORD record
ord-fbe85d4c86b0479e9378355717f3ce05
Source dataset
uspto-grants-2004_11
Patent number
US06825219B2

Reaction notes

Loading…