Methanol → HCID 66738155, compound

HRID 557734Notes

Reaction equation

HRID 557734 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]=[C:11](C(O)=O)[C:10]([C:16]([F:19])([F:18])[F:17])=[N:9]1.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.[C:44]([O:48][C:49]([N:51]1[CH2:56][CH2:55][CH:54]([C:57]2[CH:62]=[CH:61][C:60]([NH2:63])=[CH:59][CH:58]=2)[CH2:53][CH2:52]1)=[O:50])([CH3:47])([CH3:46])[CH3:45].C(N(C(C)C)CC)(C)C.[CH3:73][OH:74]>C(Cl)Cl>[C:44]([O:48][C:49]([N:51]1[CH2:56][CH2:55][CH:54]([C:57]2[CH:62]=[CH:61][C:60]([NH:63][C:73]([C:10]3([C:16]([F:17])([F:18])[F:19])[CH:11]=[CH:12][N:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])[NH:9]3)=[O:74])=[CH:59][CH:58]=2)[CH2:53][CH2:52]1)=[O:50])([CH3:47])([CH3:45])[CH3:46]

Participants

7

Reactant 5

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 21940085tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylateHCID 57652025HCID 57652025, compound

Product 1

HCID 66738155HCID 66738155, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-(2-chloro-phenyl)-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid described above (320 mg, 1.10 mmol) in methylene chloride (10 mL) was added bromotrispyrrolidinophosphonium hexafluorophosphate (770 mg, 1.65 mmol). The reaction was stirred for 10 minutes and then 4-(4-amino-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (320 mg, 1.10 mmol) followed by diisopropylethylamine (0.60 mL, 3.30 mmol) were added. The reaction was stirred at room temperature overnight. The crude mixture was diluted in methanol (100 mL), loaded onto silica gel and purified using Isco chromatography (eluting with ethyl acetate and hexanes) to give 4-(4-{[1-(2-chloro-phenyl)-3-trifluoromethyl-1H-pyrazole-carbonyl]-amino}-phenyl)-piperidine-1-carboxylic acid tert-butyl ester. The NMR spectrum obtained on the sample is compatible with its structure.

Workup

  1. additionwere added
  2. stirringThe reaction was stirred at room temperature overnight
  3. custompurified
  4. washIsco chromatography (eluting with ethyl acetate and hexanes)

Sources & evidence

ORD record
ord-b0d95f34ca5640efa757b7681a8267d1
Source dataset
uspto-grants-2011_11
Patent number
US08058299B2

Reaction notes

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