3-Quinolinecarboxylic acid, 4-chloro-8-methoxy-, ethyl ester → HCID 67250705, compound

HRID 1752762Notes

Reaction equation

HRID 1752762 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH3:18])=[O:5])[CH3:2].[C:19]([O:23][C:24]([N:26]1[CH2:30][CH2:29][C@@H:28]([NH2:31])[CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:31][C@@H:28]1[CH2:29][CH2:30][N:26]([C:24]([O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:25])[CH2:27]1)=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH3:18])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 3045573-Quinolinecarboxylic acid, 4-chloro-8-methoxy-, ethyl esterHCID 854070(R)-(+)-1-Boc-3-aminopyrrolidine

Product 1

HCID 67250705HCID 67250705, compound

Procedure

4-Chloro-8-methoxy-quinoline-3-carboxylic acid ethyl ester (266 mg, 1.0 mmol) was treated with (R)-3-amino-pyrrolidine-1-carboxylic acid tert-butyl ester following general procedure B to afford 4-((R)-1-tert-butoxycarbonyl-pyrrolidin-3-ylamino)-8-methoxy-quinoline-3-carboxylic acid ethyl ester 381 mg). Thus obtained amino-ester (208 mg, 0.5 mmol) was subjected to reaction with 1-chloro-3-isocyanato-benzene according to general procedure C to furnish 3-[(R)-3-(3-chloro-phenyl)-7-methoxy-2,4-dioxo-3,4-dihydro-2H-pyrimido[5,4-c]quinolin-1-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester (194 mg). LCMS: m/z 523 [M+1]+.

Sources & evidence

ORD record
ord-2c9f074c787941149808dc335c9be560
Source dataset
uspto-grants-2015_10
Patent number
US09163022B2

Reaction notes

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