Hydrochloric Acid → HCID 118389985, compound

HRID 1478024Notes

Reaction equation

HRID 1478024 reaction equation
[Cl:1][C:2]1[C:3]([N:15]([CH3:34])[CH:16]2[CH2:33][CH2:32][C:19]3([CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]3)[CH2:18][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.Cl.CCOC(C)=O.C([O-])(O)=O.[Na+]>ClCCl.O.C(Cl)Cl.CO>[Cl:1][C:2]1[C:3]([N:15]([CH3:34])[CH:16]2[CH2:33][CH2:32][C:19]3([CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[CH2:18][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

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 118390068HCID 118390068, compound

Product 1

HCID 118389985HCID 118389985, compoundYield 65.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 21226129Dichloromethane methanolSolvent

Procedure

To a suspension of tert-butyl 9-((5-chloro-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)(methyl)amino)-3-azaspiro[5.5]undecane-3-carboxylate (330 mg, 0.67 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 and then adjust to pH=8-9 with the solution of saturated NaHCO3. The resulting mixture was diluted with 20 mL of H2O and exacted with a mixture of DCM and MeOH (10/1, 10 mL×3). The combine organic layers were washed with brine (20 mL×1), then 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 (170 mg, 64.8%).

Workup

  1. washThe combine organic layers were washed with brine (20 mL×1)
  2. filtrationover Na2SO4, filtered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash silica gel column chromatography (DCM/MeOH (v/v)=10/1 to 5/1)

Sources & evidence

ORD record
ord-8cf19f2eb46e47b4b207ca5b8afb528a
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

Loading…