Trifluoroacetic acid → HCID 118390053, compound

HRID 1477997Notes

Reaction equation

HRID 1477997 reaction equation
[Cl:1][C:2]1[C:3]([NH:15][CH:16]2[C:20]3([CH2:24][CH2:23][CH2:22][CH2:21]3)[CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17]2)=[N:4][C:5]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)=[N:6][CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[C:3]([NH:15][CH:16]2[C:20]3([CH2:21][CH2:22][CH2:23][CH2:24]3)[CH2:19][NH:18][CH2:17]2)=[N:4][C:5]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118390058HCID 118390058, compound

Product 1

HCID 118390053HCID 118390053, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-((5-chloro-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)-2-azaspiro[4.4]nonane-2-carboxylate (650 mg, 1.45 mmol) in DCM (20 mL) was added CF3COOH (5 mL) and the reaction mixture was stirred at rt for 2 hours. The reaction mixture was concentrated in vacuo and adjusted to pH=8-9 with a saturated Na2CO3 solution, then the mixture was diluted with H2O (20 mL) and extracted with 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)=10/1 to 5/1) to give the product as a white solid (490 mg, 97%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe mixture was diluted with H2O (20 mL)
  3. extractionextracted with EtOAc (50 mL×3)
  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)=10/1 to 5/1)

Sources & evidence

ORD record
ord-c5ed30de28664e58bf98b41dd042bc2b
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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