Hydrochloric Acid → HCID 178489134, compound

HRID 735406Notes

Reaction equation

HRID 735406 reaction equation
F[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)=O.O.[NH2:23][NH2:24].CCOC(C)=O.Cl>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]2[C:3]3[C:2](=[C:7]([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:5][CH:4]=3)[NH:24][N:23]=2)=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 24654Hydrazine hydrate (1:1)HCID 11231817(2-Fluoro-3-trifluoromethyl-phenyl)-(4-methoxy-phenyl)-methanone

Product 1

HCID 178489134HCID 178489134, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

(2-Fluoro-3-trifluoromethyl-phenyl)-(4-methoxy-phenyl)-methanone (59.6 mg, 0.2 mmol) was dissolved in 1 ml of pyridine. Hydrazine hydrate (97 μl, 2 mmol) and 4-(dimethylamino)-pyridine (24.4 mg, 0.2 mmol) were added. The reaction mixture was stirred overnight at 100° C. After cooling to room temperature, EtOAc and 1M HCl were added. The organic phase was washed three times with brine, dried over MgSO4 and concentrated under vacuum. Purification of the crude product by flash column chromatography on silica gel (n-heptane/ethyl acetate, 85:15) afforded 56 mg of the analytically pure product.

Workup

  1. temperatureAfter cooling to room temperature
  2. washThe organic phase was washed three times with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under vacuum
  5. customPurification of the crude product by flash column chromatography on silica gel (n-heptane/ethyl acetate, 85:15)
  6. customafforded 56 mg of the analytically pure product

Sources & evidence

ORD record
ord-e5b002c7829a48b59466c67f9f54788a
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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