Hydrochloric Acid → HCID 118390117, compound

HRID 1478006Notes

Reaction equation

HRID 1478006 reaction equation
[Cl:1][C:2]1[C:3]([N:15]([CH3:33])[CH:16]2[CH2:20][CH2:19][C:18]3([CH2:25][CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21]3)[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(Cl)Cl>[Cl:1][C:2]1[C:3]([N:15]([CH3:33])[CH:16]2[CH2:20][CH2:19][C:18]3([CH2:25][CH2:24][CH2:23][NH:22][CH2:21]3)[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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 118390011HCID 118390011, compound

Product 1

HCID 118390117HCID 118390117, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-((5-chloro-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)(methyl)amino)-7-azaspiro[4.5]decane-7-carboxylate (270 mg, 0.567 mmol) in DCM (10 mL) was added a solution of HCl in EtOAc (10 mL, 40 mmol). The reaction mixture was stirred at rt overnight and concentrated in vacuo. The residue was dissolved in water (30 mL) and adjusted to pH=10 with a saturated Na2CO3 aqueous solution, then extracted with DCM (100 mL×3). The combined organic phases were washed with brine (100 mL), then dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (NH3 in MeOH (7 M)/MeOH/DCM (v/v/v)=1/20/60) to give the title compound as a beige solid (0.20 g, 93.8%).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water (30 mL)
  3. extractionextracted with DCM (100 mL×3)
  4. washThe combined organic phases were washed with brine (100 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (NH3 in MeOH (7 M)/MeOH/DCM (v/v/v)=1/20/60)

Sources & evidence

ORD record
ord-cf945d73063a4dd7aee81df54fd17dd5
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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