Trifluoroacetic acid → HCID 71116108, compound

HRID 2276899Notes

Reaction equation

HRID 2276899 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]([N:23]3[CH2:28][CH2:27][CH:26]([NH:29]C(=O)OC(C)(C)C)[CH2:25][CH2:24]3)=[O:22])[C:9]=2[CH3:37])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]([N:23]3[CH2:24][CH2:25][CH:26]([NH2:29])[CH2:27][CH2:28]3)=[O:22])[C:9]=2[CH3:37])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86716055HCID 86716055, compound

Product 1

HCID 71116108HCID 71116108, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl N-(1-{[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]carbonyl}piperidin-4-yl)carbamate (194 mg) was stirred in dichloromethane (7 mL) and trifluoroacetic acid (3 mL) for 4 h. The reaction was concentrated in vacuo and dissolved in ethyl acetate. The solution was washed with 3.8 N NaOH and brine. The organic layer was dried with magnesium sulfate. The reaction was concentrated in vacuo to yield 0.15 g (94%) of desired product. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.31-1.52 (m, 2H) 1.83-2.02 (m, 2H) 2.14-2.26 (m, 3H) 2.84-3.07 (m, 2H) 3.11-3.33 (m, 1H) 4.31 (d, J=13.47 Hz, 1H) 4.66 (d, J=13.19 Hz, 1H) 7.07 (d, J=8.38 Hz, 2H) 7.14-7.20 (m, 1H) 7.21-7.34 (m, 3H) 7.44 (d, J=1.98 Hz, 1H); [M+H]+ 463.4.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutiondissolved in ethyl acetate
  3. washThe solution was washed with 3.8 N NaOH and brine
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-1f2997042cc7498f8cf01dfa431c7dee
Source dataset
uspto-grants-2015_09
Patent number
US09133128B2

Reaction notes

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