Hydrochloric Acid → HCID 118410729, compound

HRID 1477967Notes

Reaction equation

HRID 1477967 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[CH2:31][CH2:30][C:18]4([CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]4)[CH2:17][CH2:16]3)[CH:11]=[CH:10][N:9]=2)[CH:4]=[N:3]1.Cl.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.CCOC(C)=O.O>[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]2[N:13]=[C:12]([NH:14][CH:15]3[CH2:31][CH2:30][C:18]4([CH2:22][NH:21][CH2:20][CH2:19]4)[CH2:17][CH2:16]3)[CH:11]=[CH:10][N:9]=2)[CH:4]=[N:3]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 118390030HCID 118390030, compound

Product 1

HCID 118410729HCID 118410729, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 8-((2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)-2-azaspiro[4.5]decane-2-carboxylate (0.51 g, 1.19 mmol) in DCM (10 mL) was added a solution of HCl in EtOAc (5 mL, 2.83 M) and the mixture was stirred at rt for 16 h. The reaction mixture was diluted with water (10 mL) and adjusted to pH=8 with saturated Na2CO3 solution, then extracted with DCM (20 mL×3), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=10/1) to give the product as a yellow solid (0.17 g, 44%).

Workup

  1. extractionextracted with DCM (20 mL×3)
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=10/1)

Sources & evidence

ORD record
ord-72ce07281ec64f5886dc3fd49bbda9eb
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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