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Quinoline → 2-Chloro-N-cyclopropyl-4-[(1Z)-3-oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-amino)prop-1-en-1-yl]benzamide

HRID 339126
Notes
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Reaction equation

HRID 339126 reaction equation
[Cl:1][C:2]1[CH:13]=[C:12]([C:14]#[C:15][C:16](=[O:33])[NH:17][CH:18]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=2)[C:19]([F:22])([F:21])[F:20])[CH:11]=[CH:10][C:3]=1[C:4]([NH:6][CH:7]1[CH2:9][CH2:8]1)=[O:5].N1C2C(=CC=CC=2)C=CC=1>CO.[Pd]>[Cl:1][C:2]1[CH:13]=[C:12](/[CH:14]=[CH:15]\[C:16](=[O:33])[NH:17][CH:18]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:30])([F:31])[F:32])[CH:24]=2)[C:19]([F:22])([F:20])[F:21])[CH:11]=[CH:10][C:3]=1[C:4]([NH:6][CH:7]1[CH2:8][CH2:9]1)=[O:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 7047QuinolineHCID 582479322-Chloro-N-cyclopropyl-4-[3-oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}amino)-prop-1-yn-1-yl]benzamide

Product 1

HCID 866530762-Chloro-N-cyclopropyl-4-[(1Z)-3-oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-amino)prop-1-en-1-yl]benzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×
HCID 887
Methanol
Solvent

Procedure

2-Chloro-N-cyclopropyl-4-[3-oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}amino)-prop-1-yn-1-yl]benzamide (110 mg, 0.20 mmol), quinoline (10 mg, 0.07 mmol) and palladium on calcium carbonate (5% Pd; 10 mg) were suspended in methanol and stirred for 4 days, in the course of which palladium on calcium carbonate (3×10 mg) was added again every 24 h. Then the reaction mixture was filtered through kieselguhr, and the filtrate concentrated to dryness under reduced pressure. The residue was purified by means of silica gel chromatography with the eluent cyclohexane/ethyl acetate (EA) (0% EA to 50% EA).

Workup

  1. additionwas added again every 24 h
  2. filtrationThen the reaction mixture was filtered through kieselguhr
  3. concentrationthe filtrate concentrated to dryness under reduced pressure
  4. customThe residue was purified by means of silica gel chromatography with the eluent cyclohexane/ethyl acetate (EA) (0% EA to 50% EA)

Sources & evidence

ORD record
ord-7709bf0289f947ed8e9b54ddb59d0ef8
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08889878B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes