2-Isocyanato-4-methylthiophene → 1-Cyclopentyl-7-methoxy-3-(4-methyl-thiophen-2-yl)-1H-pyrimido[5,4-c]quinoline-2,4-dione

HRID 1053040Notes

Reaction equation

HRID 1053040 reaction equation
C(O[C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)=[CH:13][CH:12]=[CH:11][C:10]=2[O:22][CH3:23])=[O:5])C.[N:24]([C:27]1[S:28][CH:29]=[C:30]([CH3:32])[CH:31]=1)=[C:25]=[O:26]>>[CH:17]1([N:16]2[C:15]3[C:14]4[CH:13]=[CH:12][CH:11]=[C:10]([O:22][CH3:23])[C:9]=4[N:8]=[CH:7][C:6]=3[C:4](=[O:5])[N:24]([C:27]3[S:28][CH:29]=[C:30]([CH3:32])[CH:31]=3)[C:25]2=[O:26])[CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

3

Reactant 2

HCID 71278012-Isocyanato-4-methylthiopheneHCID 672497184-Cyclopentylamino-8-methoxy-quinoline-3-carboxylic acid ethyl ester

Product 1

HCID 583294731-Cyclopentyl-7-methoxy-3-(4-methyl-thiophen-2-yl)-1H-pyrimido[5,4-c]quinoline-2,4-dioneYield 63.8%

Procedure

1-Cyclopentyl-7-methoxy-3-(4-methyl-thiophen-2-yl)-1H-pyrimido[5,4-c]quinoline-2,4-dione (26 mg) was prepared from 4-cyclopentylamino-8-methoxy-quinoline-3-carboxylic acid ethyl ester (0.1 mmol) and 2-isocyanato-4-methyl-thiophene (0.5 mmol) following general procedure C. LCMS: m/z 408 [M+1]+. 1H NMR (400 MHz, CDCl3): δ 9.44 (s, 1H), 8.32 (s, 1H), 7.80 (d, 1H), 7.63 (t, 1H), 7.28 (d, 1H), 6.89 (s, 1H), 5.05 (p, 1H), 4.10 (s, 3H), 3.02 (s, 3H), 2.29 (m, 2H), 2.11-2.19 (m, 4H), 1.25 (m, 2H) ppm.

Sources & evidence

ORD record
ord-d342c9f07a34422f9dbef6ccd0c28b3f
Source dataset
uspto-grants-2016_07
Patent number
US09393245B2

Reaction notes

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