N-methyl-2-pyrrolidone → HCID 86661294, compound

HRID 1685032Notes

Reaction equation

HRID 1685032 reaction equation
CN1CCCC1=O.[NH2:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:13]=1.[F:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][N:29]=[C:30]=[O:31])[CH:23]=1>O>[F:21][C:22]1[CH:23]=[C:24]([CH:25]=[CH:26][CH:27]=1)[CH2:28][NH:29][C:30](=[O:31])[NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:13]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 6434993-Fluorobenzyl isocyanateHCID 4356513Ethyl 2-(2-Amino-4-thiazolyl)-2-oxoacetate

Product 1

HCID 86661294HCID 86661294, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An N-methylpyrrolidinone (5 mL) solution of ethyl 2-(2-aminothiazol-4-yl)-2-oxoacetate (commercial, 1.00 g, 5.0 mmol) and 1-fluoro-3-(isocyanatomethyl)benzene (831 mg, 5.5 mmol) was heated in a microwave reactor at 120 C for 30 minutes. Upon cooling, water (50 mL) was added with vigorous stiffing. Filtration of the precipitate afforded ethyl 2-(2-(3-(3-fluorobenzyl)ureido)thiazol-4-yl)-2-oxoacetate. M/Z 352 (M+H)+. The filtrate was dissolved in EtOH (100 mL) then hydroxylamine hydrochloride (700 mg, 10 mmol) and sodium acetate (1.07 g, 13 mmol) were added to the mix. The solution was stirred at 75 C for 4 hours and filtered while hot. Evaporation of the mixture and Flash chromatography afforded ethyl 2-(2-(3-(3-fluorobenzyl)ureido)thiazol-4-yl)-2-(hydroxyimino)acetate as a mixture of isomers. M/Z 367 (M+H)+.

Workup

  1. temperatureUpon cooling
  2. filtrationFiltration of the precipitate

Sources & evidence

ORD record
ord-a3c9b17b3b724ba2b48b6e3938ec1412
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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