HCID 86675133, compound → HCID 86675132, compound

HRID 1502672Notes

Reaction equation

HRID 1502672 reaction equation
[CH:1]1([C:4]([NH:6][NH:7][C:8](=O)[CH2:9][NH:10][C:11](=[O:34])[C:12]2[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[CH:20]([C:25]3[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=3)[C:21]([F:24])([F:23])[F:22])=[CH:14][C:13]=2[CH3:33])=[O:5])[CH2:3][CH2:2]1>O=P(Cl)(Cl)Cl>[CH:1]1([C:4]2[O:5][C:8]([CH2:9][NH:10][C:11](=[O:34])[C:12]3[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[CH:20]([C:25]4[CH:26]=[C:27]([Cl:32])[CH:28]=[C:29]([Cl:31])[CH:30]=4)[C:21]([F:22])([F:24])[F:23])=[CH:14][C:13]=3[CH3:33])=[N:7][N:6]=2)[CH2:2][CH2:3]1

Participants

3

Reactant 1

HCID 86675133HCID 86675133, compound

Product 1

HCID 86675132HCID 86675132, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of (E)-N-(2-(2-(cyclopropanecarbonyl)hydrazinyl)-2-oxoethyl)-4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-enyl)-2-methylbenzamide (200 mg, 0.379 mmol) in POCl3 (2.0 mL) was stirred at ambient temperature for 10 min, then the resultant reaction mixture was heated to 50° C. for 1 h. The reaction mixture was quenched with ice water at 0° C. and extracted with ethyl acetate. The combined ethyl acetate layer was washed with saturated NaHCO3 solution and brine solution, dried over anhydrous Na2SO4, and concentrated under reduced pressure. Purification by flash column chromatography (SiO2, 100-200 mesh; eluting with 50% ethyl acetate/pet ether) afforded the title compound as a light brown gummy material (70.0 mg, 36%): 1H NMR (400 MHz, CDCl3) δ 7.43 (m, 2H), 7.27 (m, 2H), 7.23 (m, 2H), 6.58 (d, J=16.0 Hz, 1H), 6.41 (dd, J=16.0, 7.6 Hz, 1H), 4.79 (d, J=5.6 Hz, 2H), 4.14 (m, 1H), 2.48 (s, 3H), 2.18 (m, 1H), 1.16 (m, 4H); ESIMS m/z 509.89 ([M+H]+); IR (thin film) 1666, 1166, 1112, 800 cm−1.

Workup

  1. customthe resultant reaction mixture
  2. customThe reaction mixture was quenched with ice water at 0° C.
  3. extractionextracted with ethyl acetate
  4. washThe combined ethyl acetate layer was washed with saturated NaHCO3 solution and brine solution
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customPurification
  8. washby flash column chromatography (SiO2, 100-200 mesh; eluting with 50% ethyl acetate/pet ether)

Sources & evidence

ORD record
ord-c9ce77fe3ce048ea9cdcdb9f71361524
Source dataset
uspto-grants-2015_12
Patent number
US09210927B2

Reaction notes

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