Oxygen → HCID 58345426, compound

HRID 1877991Notes

Reaction equation

HRID 1877991 reaction equation
O=O.FC(F)(F)C(O)=O.[Cl:10][C:11]1[CH:12]=[C:13]([N:17]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:32])([F:31])[F:30])[CH:23]=3)=[CH:20][C:19]([C:33]([N:35]3[CH2:40][CH2:39][N:38](C(OC(C)(C)C)=O)[CH2:37][CH2:36]3)=[O:34])=[N:18]2)[CH:14]=[CH:15][CH:16]=1.ClC1C=C(N2C(C3C=CC=C(OC(F)(F)F)C=3)=CC(C(O)=O)=N2)C=CC=1.N1(C(OC(C)(C)C)=O)CCNCC1>ClCCl>[Cl:10][C:11]1[CH:12]=[C:13]([N:17]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:31])([F:30])[F:32])[CH:23]=3)=[CH:20][C:19]([C:33]([N:35]3[CH2:36][CH2:37][NH:38][CH2:39][CH2:40]3)=[O:34])=[N:18]2)[CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 5

HCID 977OxygenHCID 6422Trifluoroacetic acidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 58277445HCID 58277445, compoundHCID 58345404HCID 58345404, compound

Product 1

HCID 58345426HCID 58345426, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under exclusion of oxygen, 5 ml of dichloromethane and 1 ml of trifluoroacetic acid were added to 140 mg (0.25 mmol) of tert-butyl 4-{[1-(3-chlorophenyl)-5-(3-trifluoromethoxy-phenyl)-1H-pyrazol-3-yl]carbonyl}piperazine-1-carboxylate, prepared from the compound of example 9A and tert-butyl piperazine-1-carboxylate in analogy to example 1, and the mixture is stirred for 12 hours at room temperature. The reaction mixture is diluted with dichloromethane and washed with a sodium bicarbonate solution and a sodium chloride solution. The organic phase is dried over sodium sulfate and concentrated on a rotary evaporator. 101 mg (88% yield of theory) of product are obtained. By thorough drying in high vacuum at 60° C. an analytical sample is freed of solvent residues.

Workup

  1. washwashed with a sodium bicarbonate solution
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. concentrationconcentrated on a rotary evaporator
  4. custom101 mg (88% yield of theory) of product are obtained
  5. customBy thorough drying in high vacuum at 60° C. an analytical sample

Sources & evidence

ORD record
ord-a9791154fb3a4ec09b6853f8b8f736ed
Source dataset
uspto-grants-2012_11
Patent number
US08314089B2

Reaction notes

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