3-Quinolinecarboxylic acid, 4-chloro-8-methoxy-, ethyl ester → HCID 67250182, compound

HRID 533079

Reaction equation

HRID 533079 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].[F:19][C:20]1([F:27])[CH2:25][CH2:24][CH:23]([NH2:26])[CH2:22][CH2:21]1>>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:26][CH:23]1[CH2:24][CH2:25][C:20]([F:27])([F:19])[CH2:21][CH2:22]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 3847030(4,4-Difluorocyclohexyl)amine

Product 1

HCID 67250182HCID 67250182, compound

Procedure

4-Chloro-8-methoxy-quinoline-3-carboxylic acid ethyl ester (250 mg, 0.94 mmol) was treated with 4,4-difluoro-cyclohexylamine following general procedure B to afford 4-(4,4-difluoro-cyclohexylamino)-8-methoxy-quinoline-3-carboxylic acid ethyl ester (192 mg). Thus obtained amino-ester (92 mg, 0.25 mmol) was subjected to reaction with 1-chloro-3-isocyanato-benzene according to general procedure C to furnish 3-(3-chloro-phenyl)-1-(4,4-difluoro-cyclohexyl)-7-methoxy-1H-pyrimido[5,4-c]quinoline-2,4-dione (69 mg). LCMS: m/z 472 [M+1]+. 1H NMR (400 MHz, CDCl3): δ 9.56 (s, 1H), 7.58 (m, 1H), 7.48 (m, 1H), 7.38 (m, 1H), 7.24 (m, 1H), 7.06-7.14 (m, 2H), 6.48 (m, 1H), 5.09 (m, 1H), 4.08 (s, 3H), 2.84 (m, 2H), 2.23 (m, 2H), 1.80-2.00 (m, 4H) ppm.

Sources & evidence

ORD record
ord-7aa4326d6c4a4a73b01d1e8d68f0ea5d
Source dataset
uspto-grants-2014_10
Patent number
US08853226B2

Linked notes

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