3-(2-Chloro-6-fluorophenyl)-5-methylisoxazole-4-carbonyl chloride → Methyl-N-(3-[2-Chloro-6-Fluorophenyl]-5-Methylisoxazol-4-oyl)-4-Aminobutanoate

HRID 2228475Notes

Reaction equation

HRID 2228475 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[CH2:5][CH2:6][CH2:7][NH2:8].[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=1[C:18]1[C:22]([C:23](Cl)=[O:24])=[C:21]([CH3:26])[O:20][N:19]=1>>[CH3:2][O:3][C:4](=[O:9])[CH2:5][CH2:6][CH2:7][NH:8][C:23]([C:22]1[C:18]([C:12]2[C:13]([F:17])=[CH:14][CH:15]=[CH:16][C:11]=2[Cl:10])=[N:19][O:20][C:21]=1[CH3:26])=[O:24]

Participants

3

Reactant 2

HCID 27365813-(2-Chloro-6-fluorophenyl)-5-methylisoxazole-4-carbonyl chlorideHCID 27563834-Aminobutyric acid methyl ester hydrochloride

Product 1

HCID 18470609Methyl-N-(3-[2-Chloro-6-Fluorophenyl]-5-Methylisoxazol-4-oyl)-4-AminobutanoateYield 103.9%

Procedure

Methyl-4-aminobutanoate hydrochloride (668 mg, 4.34 mmol) and 3-(2-chloro-6-fluorophenyl)-5-methylisoxazol-4-oyl chloride (1.19 g, 4.35 mmol) were converted to 1.60 g of the title compound by the procedure of Preparation 1 except that the residue was not treated with hexanes. (100%). EA calculated for: C16H16N2O4ClF: C, 54.17; H, 4.55; N, 7.90. Found: C, 54.41; H, 4.58; N, 7.78. MS(FD) m/z 355 (M+).

Sources & evidence

ORD record
ord-9fb430530d7a44e387dbd0fb0590be3a
Source dataset
uspto-grants-2002_07
Patent number
US06417193B1

Reaction notes

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