Benzoyl chloride, 3,4,5-trimethoxy- → HCID 25232900, compound

HRID 419907Notes

Reaction equation

HRID 419907 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]2[N:11]([CH:12]=1)[CH:10]=[C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH2:19])[S:8]2)=[O:4].[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32])[C:25](Cl)=[O:26]>N1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]2[N:11]([CH:12]=1)[CH:10]=[C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH:19][C:25](=[O:26])[C:24]1[CH:23]=[C:22]([O:21][CH3:20])[C:30]([O:31][CH3:32])=[C:29]([O:33][CH3:34])[CH:28]=1)[S:8]2)=[O:4]

Participants

4

Reactant 2

HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 25232899HCID 25232899, compound

Product 1

HCID 25232900HCID 25232900, compoundYield 243.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-(2-Amino-phenyl)-imidazo[2,1-b]thiazole-6-carboxylic acid methyl ester (27 mg, 0.095 mmol) was mixed with 1 mL of pyridine along with 22 mg of 3,4,5-trimethoxybenzoyl chloride. The reaction mixture was reacted in a microwave reactor at 160° C. for 10 minutes. It was then cooled to room temperature and concentrated. The resulting crude product was purified by preparative HPLC using a mixture of aqueous acetonitrile that has been buffered with 0.1% TFA to afford 108 mg of 2-[2-(3,4,5-trimethoxybenzoylamino)-phenyl]-imidazo[2,1-b]thiazole-6-carboxylic acid methyl ester (MS, M++H=468).

Workup

  1. customThe reaction mixture was reacted in a microwave reactor at 160° C. for 10 minutes
  2. concentrationconcentrated
  3. customThe resulting crude product was purified by preparative HPLC
  4. additiona mixture of aqueous acetonitrile that

Sources & evidence

ORD record
ord-64310bb35a1d463998e7f37052a36de0
Source dataset
uspto-grants-2012_01
Patent number
US08093401B2

Reaction notes

Loading…