2-(Isocyanatomethyl)furan → 1-Cyclopentyl-3-furan-2-ylmethyl-7-methoxy-1H-pyrimido[5,4-c]quinoline-2,4-dione

HRID 532999Notes

Reaction equation

HRID 532999 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.[O:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[CH2:29][N:30]=[C:31]=[O:32]>>[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:30]([CH2:29][C:25]3[O:24][CH:28]=[CH:27][CH:26]=3)[C:31]2=[O:32])[CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

3

Reactant 2

HCID 42238112-(Isocyanatomethyl)furanHCID 672497184-Cyclopentylamino-8-methoxy-quinoline-3-carboxylic acid ethyl ester

Product 1

HCID 441870581-Cyclopentyl-3-furan-2-ylmethyl-7-methoxy-1H-pyrimido[5,4-c]quinoline-2,4-dioneYield 53.7%

Procedure

1-Cyclopentyl-3-furan-2-ylmethyl-7-methoxy-1H-pyrimido[5,4-c]quinoline-2,4-dione (21 mg) was prepared from 4-cyclopentylamino-8-methoxy-quinoline-3-carboxylic acid ethyl ester (0.10 mmol) and (2-furyl)methyl isocyanate (0.4 mmol) following general procedure C. LCMS: m/z 392 [M+1]+. 1H NMR (400 MHz, CDCl3): δ 9.45 (s, 1H), 7.78 (d, 1H), 7.57 (t, 1H), 7.32 (d, 1H), 7.24 (d, 1H), 6.30 (d, 1H), 6.18 (d, 1H), 5.04 (p, 1H), 4.33 (s, 2H), 4.12 (s, 3H), 2.40 (m, 2H), 2.11 (m, 4H), and 1.16 (m, 2H) ppm.

Sources & evidence

ORD record
ord-535adade27744c348a42d6453a73661e
Source dataset
uspto-grants-2014_10
Patent number
US08853226B2

Reaction notes

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