Cyclopropanecarbonyl chloride → Cyclopropanecarboxylic 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 530366Notes

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.[CH:24]1([C:27](Cl)=[O:28])[CH2:26][CH2:25]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:27]([CH:24]5[CH2:26][CH2:25]5)=[O:28])[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

Reactant 2

HCID 77637Cyclopropanecarbonyl chloride

HCID 86679929(R)-6-(8-amino-5,6,7,8-tetrahydroisoquinolin-4-yl)-1-methyl-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 71538739Cyclopropanecarboxylic 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 intermediate B-1, reaction of (R)-6-(8-amino-5,6,7,8-tetrahydroisoquinolin-4-yl)-1-methyl-3,4-dihydroquinolin-2(1H)-one (example 61) with cyclopropanecarbonyl chloride gave the title compound as a light yellow solid. MS: 376.5 (M+H+).

Sources & evidence

ORD record: ord-0da9d03b40124ae5b742b383af012a21
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353081B2

Reaction notes

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