Trifluoroacetic acid → HCID 131736499, compound

HRID 1477994Notes

Reaction equation

HRID 1477994 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]2[N:13]=[C:12]([NH:14][CH:15]3[C:19]4([CH2:23][CH2:22][CH2:21][CH2:20]4)[CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16]3)[CH:11]=[CH:10][N:9]=2)[CH:4]=[N:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]2[N:13]=[C:12]([NH:14][CH:15]3[C:19]4([CH2:20][CH2:21][CH2:22][CH2:23]4)[CH2:18][NH:17][CH2:16]3)[CH:11]=[CH:10][N:9]=2)[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118390113HCID 118390113, compound

Product 1

HCID 131736499HCID 131736499, compoundYield 108%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-((2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)-2-azaspiro[4.4]nonane-2-carboxylate (550 mg, 1.33 mmol) in DCM (20 mL) was added CF3COOH (5 mL) and the reaction mixture was stirred at rt for 2 h. The reaction mixture was concentrated in vacuo and adjust to pH=8˜9 with the saturated NaHCO3 aqueous solution, then diluted with H2O (20 mL) and extracted withed EtOAc (50 mL×3). The combined organic phases were washed with brine (50 mL), then dried over Na2SO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=50/1 to 10/1) to give the product as a yellow solid (450 mg, 100%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with H2O (20 mL)
  3. extractionextracted
  4. washThe combined organic phases were washed with brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=50/1 to 10/1)

Sources & evidence

ORD record
ord-19c66575b39e48cca2886f7e38cbe236
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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