3-Quinolinecarboxylic acid, 4-chloro-8-methoxy-, ethyl ester → HCID 67249210, compound

HRID 533103Notes

Reaction equation

HRID 533103 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].[CH3:19][S:20]([CH2:23][CH2:24][NH2:25])(=[O:22])=[O:21]>>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:25][CH2:24][CH2:23][S:20]([CH3:19])(=[O:22])=[O:21])=[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 43405612-(Methylsulfonyl)ethanamine

Product 1

HCID 67249210HCID 67249210, compound

Procedure

4-Chloro-8-methoxy-quinoline-3-carboxylic acid ethyl ester (266 mg, 1.0 mmol) was treated with 2-methanesulfonyl-ethylamine following general procedure B to afford 4-(2-methanesulfonyl-ethylamino)-8-methoxy-quinoline-3-carboxylic acid ethyl ester (305 mg). Thus obtained amino-ester (70 mg, 0.2 mmol) was subjected to reaction with 5-Isocyanato-benzo[1,3]dioxole according to general procedure C to furnish 3-Benzo[1,3]dioxol-5-yl-1-(2-methanesulfonyl-ethyl)-7-methoxy-1H-pyrimido[5,4-c]quinoline-2,4-dione (43 mg). LCMS: m/z 471 [M+1]+.

Sources & evidence

ORD record
ord-cac357c29add41ada63b5a0d19e66dbe
Source dataset
uspto-grants-2014_10
Patent number
US08853226B2

Reaction notes

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