Acetic Acid → HCID 86668511, compound

HRID 1805276Notes

Reaction equation

HRID 1805276 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:13]([NH2:14])=[C:12]([C:15]2[C:16]([C:27]([F:30])([F:29])[F:28])=[N:17][N:18]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)[CH:19]=2)[O:11][N:10]=1.[C:31](O)(=[O:33])C>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:13]([NH:14][CH:31]=[O:33])=[C:12]([C:15]2[C:16]([C:27]([F:29])([F:30])[F:28])=[N:17][N:18]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)[CH:19]=2)[O:11][N:10]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 86668512HCID 86668512, compound

Product 1

HCID 86668511HCID 86668511, compoundYield 36.2%

Procedure

A solution of 130 mg (0.295 mmol) 3-(2-chloro-6-fluorophenyl)-5-[1-(3-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-4-yl]isoxazol-4-amine (example I-117) in a mixture of 1847 mg (17.4 mmol) trimethylorthoether and 1660 mg (27.7 mmol) acetic acid was stirred at r.t. for 1 h. The suspension was filtered, and the obtained white solid salts were washed on the filter with hexane. Filtrates were combined and evaporated to dryness. The residue was treated by hexane, and the extract was purified by CC on silica gel, (eluent EtOAc/hexane 1/1). The obtained fraction of the pure product (example I-141) was evaporated to give 50 mg of a light greenish oil (yield 36%). Result of LC/MS MH+: 469.04; 1H NMR (400 MHz, methanol-d4): 7.29-7.35 (m, 1H) 7.44 (s, 3H) 7.46-7.50 (m, 1H) 7.57-7.67 (m, 2H) 7.72 (s, 1H) 8.26 (s, 1H)

Workup

  1. filtrationThe suspension was filtered
  2. washthe obtained white solid salts were washed on the
  3. filtrationfilter with hexane
  4. customevaporated to dryness
  5. additionThe residue was treated by hexane
  6. customthe extract was purified by CC on silica gel, (eluent EtOAc/hexane 1/1)

Sources & evidence

ORD record
ord-acef7aa5746d4fbd84bbe19d9c259e76
Source dataset
uspto-grants-2013_01
Patent number
US08354436B2

Reaction notes

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