Methyl chloroformate → 3-ethyl-7-methoxy-1-propyl-1H-pyrimido[5,4-c]quinoline-2,4-dione
Reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][CH2:17][CH2:18][CH3:19])=[CH:13][CH:12]=[CH:11][C:10]=2[O:20][CH3:21])=[O:5])[CH3:2].C([NH-])C.Cl[C:26](OC)=[O:27]>>[CH2:1]([N:3]1[C:4](=[O:5])[C:6]2[CH:7]=[N:8][C:9]3[C:10]([O:20][CH3:21])=[CH:11][CH:12]=[CH:13][C:14]=3[C:15]=2[N:16]([CH2:17][CH2:18][CH3:19])[C:26]1=[O:27])[CH3:2]Participants
4
Procedure
4-Chloro-8-methoxy-quinoline-3-carboxylic acid ethyl ester (250 mg, 0.94 mmol) was treated with 1-aminopropane following general procedure B to afford 8-methoxy-4-propylamino-quinoline-3-carboxylic acid ethyl ester (260 mg). Thus obtained amino-ester was hydrolyzed to the corresponding acid in quantitative yield using general procedure D and then transformed into 8-methoxy-4-propylamino-quinoline-3-carboxylic acid ethylamide (200 mg) following general procedure E. The above ethylamide (0.70 mmol) was subjected to reaction with methyl chloroformate according to general procedure F to furnish 3-ethyl-7-methoxy-1-propyl-1H-pyrimido[5,4-c]quinoline-2,4-dione (26 mg). LCMS: m/z 314 [M+1]+.
Sources & evidence
- ORD record
- ord-dee03234181d418ba70a6c522e7f9cc4
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853226B2
Reaction notes
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