Cyclopentylamine → HCID 67250210, compound

HRID 2424675Notes

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

Participants

Reactant 2

HCID 2906Cyclopentylamine

HCID 29272013Ethyl 4-chloro-8-(trifluoromethoxy)quinoline-3-carboxylate

Product 1

HCID 67250210HCID 67250210, compound

Procedure

4-Chloro-8-trifluoromethoxy-quinoline-3-carboxylic acid ethyl ester (250 mg, 0.94 mmol) was treated with cyclopentylamine following general procedure B to afford 4-cyclopentylamino-8-trifluoromethoxy-quinoline-3-carboxylic acid ethyl ester (220 mg). Thus obtained amino-ester was hydrolyzed to the corresponding acid using general procedure D and then transformed into the corresponding ethylamide (180 mg) following general procedure E. The above ethylamide (0.54 mmol) was subjected to reaction with methyl chloroformate according to general procedure F to furnish 1-cyclopentyl-3-ethyl-7-trifluoromethoxy-1H-pyrimido[5,4-c]quinoline-2,4-dione (60 mg). LCMS: m/z 394 [M+1]+.

Sources & evidence

ORD record: ord-8b33302e41ac431ab82ae74353e9c653
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964608B2

Reaction notes

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