N-(2-Chlorophenyl)thiourea → 8-[2-(2-chlorophenylamino)-thiazol-4-yl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

HRID 1970075

Reaction equation

HRID 1970075 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH2:11])=[S:10].Br[CH2:13][C:14]([C:16]1[CH:25]=[CH:24][C:23]2[NH:22][C:21](=[O:26])[C:20]3[NH:27][CH:28]=[CH:29][C:19]=3[C:18]=2[CH:17]=1)=O.[CH2:30]([C:32]([O-:34])=[O:33])[CH3:31]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[S:10][CH:13]=[C:14]([C:16]2[CH:25]=[CH:24][C:23]3[NH:22][C:21](=[O:26])[C:20]4[NH:27][CH:28]=[CH:29][C:19]=4[C:18]=3[CH:17]=2)[N:11]=1.[CH2:30]([C:32]([O-:34])=[O:33])[CH3:31]

Participants

4

Reactant 2

HCID 737139N-(2-Chlorophenyl)thioureaHCID 866275838-(2-bromo-acetyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

Product 1

HCID 866275878-[2-(2-chlorophenylamino)-thiazol-4-yl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylateYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

74 mg (1.2 mmol) of (2-chlorophenyl)-thiourea is added to a suspension of 124 mg (0.33 mmol) of 8-(2-bromo-acetyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in 3.5 mL of ethanol. The mixture is stirred at 90° C. for 6 hours then the mixture is cooled to room temperature. The solvent is evaporated, then the product is purified by preparative LCMS. After drying, 41 mg (27%) of 8-[2-(2-chlorophenylamino)-thiazol-4-yl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate is obtained in the form of a beige solid.

Workup

  1. temperaturethe mixture is cooled to room temperature
  2. customThe solvent is evaporated
  3. customthe product is purified by preparative LCMS
  4. customAfter drying

Sources & evidence

ORD record
ord-2970b369a8324ed38ad505a8806bc878
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Linked notes

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