Trifluoroacetic acid → HCID 66890546, compound

HRID 1897954Notes

Reaction equation

HRID 1897954 reaction equation
[C:1]([N:5]1[C:9]([NH:10][C:11]2[N:16]=[C:15]([CH2:17][C:18]3([C:37]([NH:39][NH:40]C(OC(C)(C)C)=O)=[O:38])[CH2:23][CH2:22][N:21]([C:24](=[O:36])[C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[C:26]=4[F:35])[CH2:20][CH2:19]3)[CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[C:1]([N:5]1[C:9]([NH:10][C:11]2[N:16]=[C:15]([CH2:17][C:18]3([C:37]([NH:39][NH2:40])=[O:38])[CH2:19][CH2:20][N:21]([C:24](=[O:36])[C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:32])([F:34])[F:33])[C:26]=4[F:35])[CH2:22][CH2:23]3)[CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66890859HCID 66890859, compound

Product 1

HCID 66890546HCID 66890546, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 195 mg of tert-butyl 2-((4-((6-((1-tert-butyl-1H-pyrazol-5-yl)amino)pyridin-2-yl)methyl)-1-(2-fluoro-3-(trifluoromethyl)benzoyl)piperidin-4-yl)carbonyl)hydrazinecarboxylate in 4 ml of chloroform was added 2 ml of trifluoroacetic acid at 0° C. The reaction mixture was stirred at 0° C. for 2 hours and at room temperature for 2 hours, followed by concentrating in vacuo. The resulting residue was basified with saturated aqueous sodium bicarbonate solution, and extracted with ethyl acetate. The ethyl acetate solution was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (eluent: chloroform to chloroform/methanol=10/1) to give the title compound as a colorless oil.

Workup

  1. concentrationby concentrating in vacuo
  2. extractionextracted with ethyl acetate
  3. dry with materialThe ethyl acetate solution was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customThe resulting residue was purified by a silica gel column chromatography (eluent: chloroform to chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-a329cdca615e40228024b145e9ff2929
Source dataset
uspto-grants-2013_08
Patent number
US08519136B2

Reaction notes

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