Acetic Acid → HCID 86668511, compound

HRID 2047247Notes

Reaction equation

HRID 2047247 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 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 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)
  7. customThe obtained fraction of the pure product (example 141) was evaporated

Sources & evidence

ORD record
ord-6ec6b200bc4148a781aa5695a567e15d
Source dataset
uspto-grants-2013_11
Patent number
US08592456B2

Reaction notes

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