Triethylamine → 4-oxo-8-(2-phenylamino-thiazol-4-yl)-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

HRID 1970074

Reaction equation

[C:1]1([NH:7][C:8]([NH2:10])=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:12][C:13]([C:15]1[CH:24]=[CH:23][C:22]2[NH:21][C:20](=[O:25])[C:19]3[NH:26][CH:27]=[CH:28][C:18]=3[C:17]=2[CH:16]=1)=O.[CH2:29]([C:31]([O-:33])=[O:32])[CH3:30].C(N(CC)CC)C>C(O)C>[O:25]=[C:20]1[C:19]2[NH:26][CH:27]=[CH:28][C:18]=2[C:17]2[CH:16]=[C:15]([C:13]3[N:10]=[C:8]([NH:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[S:9][CH:12]=3)[CH:24]=[CH:23][C:22]=2[NH:21]1.[CH2:29]([C:31]([O-:33])=[O:32])[CH3:30]

Participants

Conditions

Temperature: 90 °C

Procedure

34 mg (1.5 mmol) of N-phenylthiourea is added to a suspension of 57 mg (0.15 mmol) of 8-(2-bromo-acetyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in 3 mL of ethanol. The mixture is stirred at 90° C. for 48 hours then the mixture is cooled to room temperature. Triethylamine (2 mmol) is added, then the solvent is evaporated and the product is purified by chromatography on silica (chloroform/methanol/triethylamine 8/2/1). After drying, 11 mg (17%) of 4-oxo-8-(2-phenylamino-thiazol-4-yl)-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate is obtained in the form of a beige solid.

Workup

temperaturethe mixture is cooled to room temperature
customthe solvent is evaporated
customthe product is purified by chromatography on silica (chloroform/methanol/triethylamine 8/2/1)
customAfter drying

Sources & evidence

ORD record: ord-57d4c5874a3e47b785455dd384764b16
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426437B2

Linked notes

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