Ethyl isocyanate → HCID 58329414, compound

HRID 1752693Notes

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]([CH3:19])[CH3:18])=[CH:13][CH:12]=[CH:11][C:10]=2[O:20][CH3:21])=[O:5])C.[CH2:22]([N:24]=[C:25]=[O:26])[CH3:23]>>[CH2:22]([N:24]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]([CH:17]([CH3:18])[CH3:19])[C:25]1=[O:26])[CH3:23]

Participants

Reactant 2

HCID 8022Ethyl isocyanate

HCID 67248987HCID 67248987, compound

Product 1

HCID 58329414HCID 58329414, compoundYield 44.7%

Procedure

4-Chloro-8-methoxy-quinoline-3-carboxylic acid ethyl ester (267 mg, 1.0 mmol) was treated with isopropylamine (1.5 mmol) following general procedure B to afford 4-isopropylamino-8-methoxy-quinoline-3-carboxylic acid ethyl ester (256 mg). 3-Ethyl-1-isopropyl-7-methoxy-1H-pyrimido[5,4-c]quinoline-2,4-dione (14 mg) was prepared from 4-isopropylamino-8-methoxy-quinoline-3-carboxylic acid ethyl ester (0.10 mmol) and ethyl isocyanate (0.4 mmol) following general procedure C. LCMS: m/z 314 [M+1]+.

Sources & evidence

ORD record: ord-f9df19c7eabe42cc9fafcbafe92537bb
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163022B2

Reaction notes

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