Ethanesulfonyl chloride → (rac)-N-(4-(1-Methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)ethanesulfonamide

HRID 530350Notes

Reaction equation

HRID 530350 reaction equation
[NH2:1][CH:2]1[C:6]2[CH:7]=[N:8][CH:9]=[C:10]([C:11]3[CH:12]=[C:13]4[C:18](=[CH:19][CH:20]=3)[N:17]([CH3:21])[C:16](=[O:22])[CH2:15][CH2:14]4)[C:5]=2[CH2:4][CH2:3]1.[CH2:23]([S:25](Cl)(=[O:27])=[O:26])[CH3:24]>>[CH3:21][N:17]1[C:18]2[C:13](=[CH:12][C:11]([C:10]3[C:5]4[CH2:4][CH2:3][CH:2]([NH:1][S:25]([CH2:23][CH3:24])(=[O:27])=[O:26])[C:6]=4[CH:7]=[N:8][CH:9]=3)=[CH:20][CH:19]=2)[CH2:14][CH2:15][C:16]1=[O:22]

Participants

3

Reactant 2

HCID 11667Ethanesulfonyl chlorideHCID 89456204(rac)-6-(7-Amino-6,7-dihydro-5H-cyclopenta[c]pyridin-4-yl)-1-methyl-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 71536228(rac)-N-(4-(1-Methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)ethanesulfonamideYield 39%

Procedure

In analogy to the procedure described for the preparation of example 4, (rac)-6-(7-amino-6,7-dihydro-5H-cyclopenta[c]pyridin-4-yl)-1-methyl-3,4-dihydroquinolin-2(1H)-one (intermediate A-4) and ethanesulfonyl chloride gave the title compound as an off-white powder in 39% yield. MS: 386.2 (M+H+).

Sources & evidence

ORD record
ord-ae4524aa7f8b4f1ba91e5405af684880
Source dataset
uspto-grants-2016_05
Patent number
US09353081B2

Reaction notes

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