Hydrochloric Acid → HCID 131736500, compound

HRID 1478020Notes

Reaction equation

HRID 1478020 reaction equation
[CH3:1][N:2]([C:21]1[C:26]([CH3:27])=[CH:25][N:24]=[C:23]([NH:28][C:29]2[CH:30]=[N:31][N:32]([CH3:34])[CH:33]=2)[N:22]=1)[CH:3]1[CH2:20][CH2:19][C:6]2([CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]2)[CH2:5][CH2:4]1.Cl.CCOC(C)=O.C([O-])(O)=O.[Na+]>ClCCl.O.C(Cl)Cl.CO>[CH3:1][N:2]([CH:3]1[CH2:20][CH2:19][C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH2:5][CH2:4]1)[C:21]1[C:26]([CH3:27])=[CH:25][N:24]=[C:23]([NH:28][C:29]2[CH:30]=[N:31][N:32]([CH3:34])[CH:33]=2)[N:22]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 118390052HCID 118390052, compound

Product 1

HCID 131736500HCID 131736500, compoundYield 68.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a suspension of tert-butyl 9-(methyl(5-methyl-2-((1-methyl-1H-pyrazol-4-yl) amino)pyrimidin-4-yl)amino)-3-azaspiro[5.5]undecane-3-carboxylate (250 mg, 0.53 mmol) in dichloromethane (15 mL) was added the solution of HCl in EtOAc (3 mL, 12 mmol). The reaction mixture was stirred at rt for 2 h. The mixture was adjust to pH=8-9 with the saturated solution of NaHCO3, then the mixture was diluted with 20 mL H2O and exacted with DCM/MeOH (10/1, 10 mL×3). The combined organic layers were washed with brine (20 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash silica gel column chromatography (DCM/MeOH (v/v)=10/1 to 5/1) to give the title compound as a yellow solid (135 mg, 68.6%).

Workup

  1. washThe combined organic layers were washed with brine (20 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash silica gel column chromatography (DCM/MeOH (v/v)=10/1 to 5/1)

Sources & evidence

ORD record
ord-1db277c1367c4eb6bbfab587f93e8b4d
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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