Hydrochloric Acid → 2-((1-methyl-1H-pyrazol-4-yl)amino)-4-((octahydrocyclopenta[c]pyrrol-5-yl)amino)pyrimidine-5-carbonitrile

HRID 1478086Notes

Reaction equation

HRID 1478086 reaction equation
[C:1]([C:3]1[C:4]([NH:16][CH:17]2[CH2:31][CH:20]3[CH2:21][N:22](C(OC(C)(C)C)=O)[CH2:23][CH:19]3[CH2:18]2)=[N:5][C:6]([NH:9][C:10]2[CH:11]=[N:12][N:13]([CH3:15])[CH:14]=2)=[N:7][CH:8]=1)#[N:2].Cl.CCOC(C)=O.C([O-])(O)=O.[Na+]>ClCCl.O>[CH3:15][N:13]1[CH:14]=[C:10]([NH:9][C:6]2[N:5]=[C:4]([NH:16][CH:17]3[CH2:31][CH:20]4[CH2:21][NH:22][CH2:23][CH:19]4[CH2:18]3)[C:3]([C:1]#[N:2])=[CH:8][N:7]=2)[CH:11]=[N:12]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 118390115tert-butyl 5-((5-cyano-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

Product 1

HCID 1183900272-((1-methyl-1H-pyrazol-4-yl)amino)-4-((octahydrocyclopenta[c]pyrrol-5-yl)amino)pyrimidine-5-carbonitrileYield 57.02%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 5-((5-cyano-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (425 mg, 1.001 mmol) in dichloromethane (30 mL) was added the solution of HCl in EtOAc (10 mL, 40 mmol), and the mixture was stirred at rt for 1 h. The mixture was diluted with water (20 mL) and adjust to pH=8-9 with saturated NaHCO3 solution and then extracted with DCM (30 mL×3). The combined organic phases were washed with brine (50 mL), dried with anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=5/1) to give the title product as a white solid (185.2 mg, 57.02%).

Workup

  1. extractionextracted with DCM (30 mL×3)
  2. washThe combined organic phases were washed with brine (50 mL)
  3. dry with materialdried with anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=5/1)

Sources & evidence

ORD record
ord-6d32903c239d4b258ece03304adf5a69
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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