5-Methylisoxazole-4-carboxylic acid → 5-Methyl-isoxazole-4-carboxylic acid [5-(7-fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-4-methyl-pyridin-3-ylmethyl]-amide

HRID 1774886Notes

Reaction equation

HRID 1774886 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[C:5]([CH3:23])=[C:6]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][C:19]=2[F:20])[N:16]([CH3:21])[C:15](=[O:22])[CH2:14][CH2:13]3)[CH:7]=[N:8][CH:9]=1.[CH3:24][C:25]1[O:29][N:28]=[CH:27][C:26]=1[C:30](O)=[O:31]>>[F:20][C:19]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][C:15](=[O:22])[N:16]2[CH3:21])=[CH:11][C:10]=1[C:6]1[C:5]([CH3:23])=[C:4]([CH2:3][NH:2][C:30]([C:26]2[CH:27]=[N:28][O:29][C:25]=2[CH3:24])=[O:31])[CH:9]=[N:8][CH:7]=1

Participants

3

Reactant 2

HCID 14252405-Methylisoxazole-4-carboxylic acidHCID 866792106-(5-Aminomethyl-4-methyl-pyridin-3-yl)-7-fluoro-1-methyl-3,4-dihydro-1H-quinolin-2-one hydrochloride

Product 1

HCID 866792365-Methyl-isoxazole-4-carboxylic acid [5-(7-fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-4-methyl-pyridin-3-ylmethyl]-amide

Procedure

In analogy to the procedure described for the preparation of example 219, 6-(5-aminomethyl-4-methyl-pyridin-3-yl)-7-fluoro-1-methyl-3,4-dihydro-1H-quinolin-2-one hydrochloride (example 226) has been coupled with 5-methyl-isoxazole-4-carboxylic acid to give the title compound as an off-white solid. MS: 409.6 (M+H+).

Sources & evidence

ORD record
ord-278f29cc4c8b4894b53212a68703fbb6
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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