Water → 2-(4-{[5-Chloro-2-{[4-(4-pyridinyl)butanoyl]amino}-4-(trifluoromethyl)phenyl]amino}phenyl)ethyl acetate

HRID 724180Notes

Reaction equation

HRID 724180 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[CH:19]=[C:18]([Cl:20])[C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=2[NH2:25])=[CH:9][CH:8]=1)(=[O:3])[CH3:2].[N:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][CH2:34][C:35](O)=[O:36])=[CH:28][CH:27]=1.CCN=C=NCCCN(C)C.O>ClCCl>[C:1]([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[CH:19]=[C:18]([Cl:20])[C:17]([C:21]([F:22])([F:23])[F:24])=[CH:16][C:15]=2[NH:25][C:35](=[O:36])[CH2:34][CH2:33][CH2:32][C:29]2[CH:28]=[CH:27][N:26]=[CH:31][CH:30]=2)=[CH:9][CH:8]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 31596254-Pyridinebutanoic acidHCID 218755552-(4-{[2-Amino-5-chloro-4-(trifluoromethyl)phenyl]amino}phenyl)ethyl acetate

Product 1

HCID 218764332-(4-{[5-Chloro-2-{[4-(4-pyridinyl)butanoyl]amino}-4-(trifluoromethyl)phenyl]amino}phenyl)ethyl acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(4-{[2-amino-5-chloro-4-(trifluoromethyl)phenyl]amino}phenyl)ethyl acetate (step 2, 250 mg, 0.67 mmol), 4-(4-pyridinyl)butanoic acid (200 mg, 1 mmol), and WSC (191 mg, 1 mmol) in dichloromethane (7 ml) was stirred at room temperature for 1.5 h. The mixture was added water (5 ml) and extracted with dichloromethane(30 ml). The organic layer was washed with brine (5 ml), then dried (Na2SO4). The solvent was removed under reduced pressure to afford the title compound as pale brown amorphous. MS (EI) m/z: 519 (M+)

Workup

  1. extractionextracted with dichloromethane(30 ml)
  2. washThe organic layer was washed with brine (5 ml)
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1817ea02b1334440aa8daf23aa8f7316
Source dataset
uspto-grants-2006_11
Patent number
US07141580B2

Reaction notes

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