Trifluoroacetic acid → HCID 57343391, compound

HRID 2276893Notes

Reaction equation

HRID 2276893 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[C:21]([CH3:22])=[C:20]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[N:19]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=3[Cl:37])[N:18]=2)=[O:16])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([C:20]2[N:19]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=3[Cl:37])[N:18]=[C:17]([C:15]([NH:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[O:16])[C:21]=2[CH3:22])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57343390HCID 57343390, compound

Product 1

HCID 57343391HCID 57343391, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl-4-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-amido]piperidine-1-carboxylate (1 eq, 531 mg, 0.941 mmol) was stirred in dichloromethane (4 mL) and trifluoroacetic acid (1 mL) for 16 h. The reaction was concentrated in vacuo. The crude reaction material was then purified by silica gel column chromatography using 0-100% CMA 80/ethyl acetate to yield pure 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-4-yl)-1H-pyrazole-3-carboxamide (415 mg, 95%). 1H NMR (300 MHz, CHLOROFORM-d) d ppm 1.44 (qd, J=11.81, 3.86 Hz, 2H) 1.92-2.08 (m, 2H) 2.37 (s, 3H) 2.64-2.85 (m, 2H) 2.98-3.21 (m, 2H) 3.92-4.19 (m, 1H) 6.85 (d, J=8.29 Hz, 1H) 7.06 (d, J=8.38 Hz, 2H) 7.28 (s, 4H) 7.43 (s, 1H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customThe crude reaction material
  3. customwas then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a8f417f28e424f4092da4fb76c4abe54
Source dataset
uspto-grants-2015_09
Patent number
US09133128B2

Reaction notes

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