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

HRID 1970076

Reaction equation

HRID 1970076 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH2:12])=[S:11])[CH:5]=[CH:6][C:7]=1[Cl:8].Br[CH2:14][C:15]([C:17]1[CH:26]=[CH:25][C:24]2[NH:23][C:22](=[O:27])[C:21]3[NH:28][CH:29]=[CH:30][C:20]=3[C:19]=2[CH:18]=1)=O.[CH2:31]([C:33]([O-:35])=[O:34])[CH3:32]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[S:11][CH:14]=[C:15]([C:17]3[CH:26]=[CH:25][C:24]4[NH:23][C:22](=[O:27])[C:21]5[NH:28][CH:29]=[CH:30][C:20]=5[C:19]=4[CH:18]=3)[N:12]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:31]([C:33]([O-:35])=[O:34])[CH3:32]

Participants

4

Reactant 2

HCID 710776N-(3,4-Dichlorophenyl)thioureaHCID 866275838-(2-bromo-acetyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

Product 1

HCID 866275898-[2-(3,4-dichlorophenylamino)-thiazol-4-yl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylateYield 14%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

87 mg (1.2 mmol) of (3,4-dichlorophenyl)-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, 23 mg (14%) of 8-[2-(3,4-dichlorophenylamino)-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-92601354ced746f1a83e3b47dedad97f
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Linked notes

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