3-Chloropyridine-2-carboxylic acid → 3-Chloro-pyridine-2-carboxylic acid {2-[5-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-yloxy]-ethyl}-amide

HRID 1774872Notes

Reaction equation

HRID 1774872 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]([CH3:22])[C:17](=[O:23])[CH2:16][CH2:15]3)[CH:9]=[N:10][CH:11]=1.[Cl:24][C:25]1[C:26]([C:31](O)=[O:32])=[N:27][CH:28]=[CH:29][CH:30]=1>>[CH3:22][N:18]1[C:19]2[C:14](=[CH:13][C:12]([C:8]3[CH:7]=[C:6]([O:5][CH2:4][CH2:3][NH:2][C:31]([C:26]4[C:25]([Cl:24])=[CH:30][CH:29]=[CH:28][N:27]=4)=[O:32])[CH:11]=[N:10][CH:9]=3)=[CH:21][CH:20]=2)[CH2:15][CH2:16][C:17]1=[O:23]

Participants

3

Reactant 2

HCID 8246323-Chloropyridine-2-carboxylic acidHCID 866791646-[5-(2-Amino-ethoxy)-pyridin-3-yl]-1-methyl-3,4-dihydro-1H-quinolin-2-one hydrochloride

Product 1

HCID 866792183-Chloro-pyridine-2-carboxylic acid {2-[5-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-yloxy]-ethyl}-amide

Procedure

In analogy to the procedure described for the preparation of example 75, 6-[5-(2-amino-ethoxy)-pyridin-3-yl]-1-methyl-3,4-dihydro-1H-quinolin-2-one hydrochloride (example 42) has been coupled with 3-chloro-pyridine-2-carboxylic acid to give the title compound as a light yellow viscous oil. MS: 437.4 (M+H+).

Sources & evidence

ORD record
ord-7b726e295f1742358691f1887ebceca9
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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