Hydrochloric Acid → 2-(4-((4-(3-azaspiro[5.5]undecan-9-ylamino)-5-chloropyrimidin-2-yl)amino)-1H-pyrazol-1-yl)ethanol

HRID 1478059Notes

Reaction equation

HRID 1478059 reaction equation
[Cl:1][C:2]1[C:3]([NH:17][CH:18]2[CH2:35][CH2:34][C:21]3([CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]3)[CH2:20][CH2:19]2)=[N:4][C:5]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH2:14][CH2:15][OH:16])[CH:13]=2)=[N:6][CH:7]=1.Cl.CCOC(C)=O>ClCCl>[CH2:22]1[C:21]2([CH2:34][CH2:35][CH:18]([NH:17][C:3]3[C:2]([Cl:1])=[CH:7][N:6]=[C:5]([NH:8][C:9]4[CH:10]=[N:11][N:12]([CH2:14][CH2:15][OH:16])[CH:13]=4)[N:4]=3)[CH2:19][CH2:20]2)[CH2:26][CH2:25][NH:24][CH2:23]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 118390091HCID 118390091, compound

Product 1

HCID 1183900472-(4-((4-(3-azaspiro[5.5]undecan-9-ylamino)-5-chloropyrimidin-2-yl)amino)-1H-pyrazol-1-yl)ethanolYield 84.77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 9-((5-chloro-2-((1-(2-hydroxyethyl)-1H-pyrazol-4-yl)amino) pyrimidin-4-yl)amino)-3-azaspiro[5.5]undecane-3-carboxylate (500 mg, 0.99 mmol) in dichloromethane (20 mL) was added a solution of HCl in EtOAc (5 mL, 20 mmol). The mixture was stirred at room temperature for 2 h and then concentrated in vacuo. The residue was dissolved in methanol (2 mL) and adjust to pH=7-8 with the solution of NaHCO3 and extracted with DCM (100 mL×3) The combined organic phases were washed with brine (100 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified with a silica gel column chromatography (MeOH/DCM (v/v)=1/10 to 1/7) to give the product as a light yellow solid (340 mg, 84.77%).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in methanol (2 mL)
  3. extractionextracted with DCM (100 mL×3) The combined organic phases
  4. washwere washed with brine (100 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified with a silica gel column chromatography (MeOH/DCM (v/v)=1/10 to 1/7)

Sources & evidence

ORD record
ord-ca4125df30784f20af28b034c751dfa2
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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