Hydrochloric Acid → HCID 136351057, compound

HRID 1022847Notes

Reaction equation

HRID 1022847 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:27]([F:30])([F:29])[F:28])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([C:20](=O)[CH2:21][CH:22]([CH3:24])[CH3:23])=[C:16]([CH3:26])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl.[NH2:32][OH:33].Cl>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:27]([F:30])([F:29])[F:28])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([C:20](=[N:32][OH:33])[CH2:21][CH:22]([CH3:24])[CH3:23])=[C:16]([CH3:26])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 53345776HCID 53345776, compound2×

Product 1

HCID 136351057HCID 136351057, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1-{4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-phenyl}-3-methyl-butan-1-one (i.e. the product of Step 2, 228 mg) in methanol (14.3 mL) was added hydroxylamine hydrochloride (38 mg) and a catalytic amount of concentrated hydrochloric acid. The mixture was stirred at 70° C. for 4 h and concentrated in vacuum. Water was added and the mixture was extracted with ethyl acetate. Combined organic layers were dried (Na2SO4) and evaporated. Flash chromatography of the residue on silica gel obtained the title compound (94 mg, 40%).

Workup

  1. concentrationconcentrated in vacuum
  2. additionWater was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialCombined organic layers were dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-32d2650b0ca3469b889c74f26cc89a5d
Source dataset
uspto-grants-2014_05
Patent number
US08722673B2

Reaction notes

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