5-Methyl-3-phenylisoxazole-4-carbonyl chloride → HCID 58946091, compound

HRID 747860Notes

Reaction equation

HRID 747860 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13](Cl)=[O:14].[CH3:16][O:17][C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][NH2:26])=[N:21][CH:20]=1>>[N:21]1[CH:20]=[CH:19][CH:24]=[CH:23][C:22]=1[CH2:25][NH2:26].[CH3:16][O:17][C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][NH:26][C:13]([C:3]2[C:4]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[N:5][O:6][C:2]=2[CH3:1])=[O:14])=[N:21][CH:20]=1

Participants

4

Reactant 2

HCID 856245-Methyl-3-phenylisoxazole-4-carbonyl chlorideHCID 10678635methyl 6-(aminomethyl)nicotinate

Product 2

HCID 195092-PyridinemethanamineHCID 58946091HCID 58946091, compoundYield 169.6%

Procedure

As described for example 1a, 5-methyl-3-phenyl-isoxazole-4-carboxylic acid chloride (0.5 g, 2.26 mmol) was converted, using 6-aminomethyl-nicotinic acid methyl ester (313 mg, 1.88 mmol) (J. Med. Chem. 2002, 45, 5005-5022), instead of 2-picolylamine, to the title compound (0.56 g, 85%) which was obtained as a white solid. MS: m/e: 352.0 [M+H]+.

Sources & evidence

ORD record
ord-fd9e19a294044d418ba112c808769b21
Source dataset
uspto-grants-2008_07
Patent number
US07399769B2

Reaction notes

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