3-Chloropyridine-2-carboxylic acid → 3-Chloro-pyridine-2-carboxylic acid [(R)-4-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-5,6,7,8-tetrahydro-isoquinolin-8-yl]-amide

HRID 530364

Reaction equation

HRID 530364 reaction equation
[NH2:1][C@H:2]1[C:11]2[CH:10]=[N:9][CH:8]=[C:7]([C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]([CH3:22])[C:17](=[O:23])[CH2:16][CH2:15]4)[C:6]=2[CH2:5][CH2:4][CH2:3]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:7]3[C:6]4[CH2:5][CH2:4][CH2:3][C@@H:2]([NH:1][C:31]([C:26]5[C:25]([Cl:24])=[CH:30][CH:29]=[CH:28][N:27]=5)=[O:32])[C:11]=4[CH:10]=[N:9][CH:8]=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 86679929(R)-6-(8-amino-5,6,7,8-tetrahydroisoquinolin-4-yl)-1-methyl-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 866799313-Chloro-pyridine-2-carboxylic acid [(R)-4-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-5,6,7,8-tetrahydro-isoquinolin-8-yl]-amide

Procedure

In analogy to the procedure described for the preparation of example 13, coupling of (R)-6-(8-amino-5,6,7,8-tetrahydroisoquinolin-4-yl)-1-methyl-3,4-dihydroquinolin-2(1H)-one (example 61) with 3-chloro-pyridine-2-carboxylic acid gave the title compound as colorless solid. MS: 447.4 (M+H+).

Sources & evidence

ORD record
ord-4461339182d9494692a9a6c347a26331
Source dataset
uspto-grants-2016_05
Patent number
US09353081B2

Linked notes

Loading…