Formic Acid → HCID 86668509, compound

HRID 1805275Notes

Reaction equation

HRID 1805275 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 IB-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 IB-48) (yield 75%). Result of LC/MS MH+: 484.82; 1H 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-89f1820990b446dd9c882282dc4e6625
Source dataset
uspto-grants-2013_01
Patent number
US08354436B2

Reaction notes

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