Thionyl Chloride → HCID 22669217, compound

HRID 1007726Notes

Reaction equation

HRID 1007726 reaction equation
[CH:1]1([N:7]2[C:11]3[CH:12]=[CH:13][C:14]([C:16](O)=[O:17])=[CH:15][C:10]=3[N:9]=[C:8]2[C:19]2[CH:23]=[CH:22][O:21][CH:20]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O=S(Cl)[Cl:26]>CN(C=O)C>[CH:1]1([N:7]2[C:11]3[CH:12]=[CH:13][C:14]([C:16]([Cl:26])=[O:17])=[CH:15][C:10]=3[N:9]=[C:8]2[C:19]2[CH:23]=[CH:22][O:21][CH:20]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 4911131-Cyclohexyl-2-(furan-3-yl)-1H-benzimidazole-5-carboxylic acid

Product 1

HCID 22669217HCID 22669217, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The carboxylic acid of example 2 (0.550 g, 1.8 mmol) was dissolved in SOCl2 (20 mL) and DMF (˜0.1 mL). The reaction mixture was stirred at room temperature for 20 h and then concentrated to dryness and co-evaporate with EtOAc to give a 1-cyclohexyl-2-furan-3-yl-1H-benzoimidazole-5-carbonyl chloride as a brown solid (580 mg). The acid chloride (0.050 g, 0.16 mmol) was dissolved in DMF (1 mL) and reacted with 1-carnosine (0.036 g, 0.159 mmol) in the presence of DIEA (82 μL, 0.476 mmol). The reaction mixture was stirred for 3 days at room temperature before it was acidified with AcOH (1 mL) and purified by reversed phase C18 preparative HPLC. The title compound of example 145 was obtained as a white solid.

Workup

  1. concentrationconcentrated to dryness and co-evaporate with EtOAc

Sources & evidence

ORD record
ord-9b5e28588a8b4d4ca1fe8cd096c9024f
Source dataset
uspto-grants-2004_09
Patent number
US06794404B2

Reaction notes

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