Methanesulfonyl chloride → N-[(R)-4-(1-Methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-5,6,7,8-tetrahydro-isoquinolin-8-yl]-methanesulfonamide

HRID 530367Notes

Reaction equation

HRID 530367 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.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>>[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][S:25]([CH3:24])(=[O:27])=[O:26])[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 31297Methanesulfonyl chlorideHCID 86679929(R)-6-(8-amino-5,6,7,8-tetrahydroisoquinolin-4-yl)-1-methyl-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 71538740N-[(R)-4-(1-Methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-5,6,7,8-tetrahydro-isoquinolin-8-yl]-methanesulfonamide

Procedure

In analogy to the procedure described for the preparation of example 4, reaction of (R)-6-(8-amino-5,6,7,8-tetrahydroisoquinolin-4-yl)-1-methyl-3,4-dihydroquinolin-2(1H)-one (example 61) with methanesulfonyl chloride gave the title compound as a colorless solid. MS: 386.5 (M+H+).

Sources & evidence

ORD record
ord-f76242fc7f604d4aa82b8e9c71dc771a
Source dataset
uspto-grants-2016_05
Patent number
US09353081B2

Reaction notes

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