Formic Acid → HCID 86668509, compound

HRID 2047246Notes

Reaction equation

HRID 2047246 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[CH:16]=[N:17][N:18]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=3)[C:19]=2[C:20]([F:23])([F:22])[F:21])[O:11][N:10]=1.O.[CH:32](O)=[O:33]>>[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:32]=[O:33])=[C:12]([C:15]2[CH:16]=[N:17][N:18]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=3)[C:19]=2[C:20]([F:21])([F:23])[F:22])[O:11][N:10]=1

Participants

4

Reactant 3

HCID 284Formic AcidHCID 962WaterHCID 86668510HCID 86668510, compound

Product 1

HCID 86668509HCID 86668509, compoundYield 75%

Procedure

3-(2-chloro-6-fluorophenyl)-5-(1-(3-chlorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazol-4-amine (example B-36) (40 mg, 0.1 mmol) was dissolved in formic acid (3 mL). The mixture was stirred at room temperature overnight. To the reaction mixture was added water. The resulting precipitate was collected, washed with water and dried under vacuum. The product was purified by pTLC (EE/PE 2:1) to give 32 mg of the desired product (example B-48) (yield 75%). Result of LC/MS MH+: 484.82; NMR (CDCl3): 6.63 (t, 1H), 7.22 (m, 1H), 7.38-7.59 (m, 6H), 8.02 (s, 1H) 8.22 (s, 1H)

Workup

  1. customThe resulting precipitate was collected
  2. washwashed with water
  3. customdried under vacuum
  4. customThe product was purified by pTLC (EE/PE 2:1)

Sources & evidence

ORD record
ord-582f3fcf1a5f495280644aa4c49d2d7f
Source dataset
uspto-grants-2013_11
Patent number
US08592456B2

Reaction notes

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