Isopropyl isocyanate → 1-Cyclopentyl-3-isopropyl-7-methoxy-1H-pyrimido[5,4-c]quinoline-2,4-dione

HRID 532996Notes

Reaction equation

HRID 532996 reaction equation
C([O:3][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)C.[CH:24]([N:27]=[C:28]=[O:29])([CH3:26])[CH3:25]>>[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:3])[N:27]([CH:24]([CH3:26])[CH3:25])[C:28]2=[O:29])[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

3

Reactant 2

HCID 61277Isopropyl isocyanateHCID 672497184-Cyclopentylamino-8-methoxy-quinoline-3-carboxylic acid ethyl ester

Product 1

HCID 583293911-Cyclopentyl-3-isopropyl-7-methoxy-1H-pyrimido[5,4-c]quinoline-2,4-dioneYield 53.8%

Procedure

1-Cyclopentyl-3-isopropyl-7-methoxy-1H-pyrimido[5,4-c]quinoline-2,4-dione (19 mg) was prepared from 4-cyclopentylamino-8-methoxy-quinoline-3-carboxylic acid ethyl ester (0.10 mmol) and isopropyl isocyanate (0.4 mmol) following general procedure C. LCMS: m/z 354 [M+1]+. 1H NMR (400 MHz, CDCl3): δ 9.45 (s, 1H), 7.78 (d, 1H), 7.57 (t, 1H), 7.24 (d, 1H), 5.21 (p, 1H), 4.93 (m, 1H), 4.14 (s, 3H), 3.83 (m, 2H), 2.38 (m, 2H), 2.08 (m, 4H), and 1.15 (d, 6H) ppm.

Sources & evidence

ORD record
ord-b61e2672e47a49f7a1448728393123d6
Source dataset
uspto-grants-2014_10
Patent number
US08853226B2

Reaction notes

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