Hydrochloric Acid → HCID 118390106, compound

HRID 1477975Notes

Reaction equation

HRID 1477975 reaction equation
[CH3:1][C:2]1[C:3]([NH:15][CH:16]2[C:20]3([CH2:24][CH2:23][CH2:22][CH2:21]3)[CH2:19][N:18](C(OC(C)(C)C)=O)[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.O.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.CCOC(C)=O>[CH3:1][C:2]1[C:3]([NH:15][CH:16]2[C:20]3([CH2:24][CH2:23][CH2:22][CH2:21]3)[CH2:19][NH: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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10340Sodium CarbonateHCID 118390028HCID 118390028, compound

Product 1

HCID 118390106HCID 118390106, compoundYield 48.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 4-((5-methyl-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)-2-azaspiro[4.4]nonane-2-carboxylate (0.35 g, 0.82 mmol) in DCM (10 mL) was added a solution of HCl in EtOAc (2.83 M, 5 mL) and the reaction mixture was stirred at rt for 16 h then added water (10 mL). The resulting mixture was adjusted to pH=8 with a saturated Na2CO3 aqueous solution, then extracted with DCM (20 mL×3). The combined organic layers were washed with brine dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=10/1) to give the product as a yellow solid (0.13 g, 48.5%).

Workup

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

Sources & evidence

ORD record
ord-f07bdd4cbaf34dd0836d6bd776070e32
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

Loading…