Hydrochloric Acid → HCID 118390008, compound

HRID 1477957Notes

Reaction equation

HRID 1477957 reaction equation
[Cl:1][C:2]1[C:3]([N:15]([CH3:33])[CH:16]2[CH2:32][CH2:31][C:19]3([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>C(Cl)Cl.CCOC(C)=O>[Cl:1][C:2]1[C:3]([N:15]([CH3:33])[CH:16]2[CH2:32][CH2:31][C:19]3([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

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118390054HCID 118390054, compound

Product 1

HCID 118390008HCID 118390008, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of tert-butyl 8-((5-chloro-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)(methyl)amino)-2-azaspiro[4.5]decane-2-carboxylate (3.9 A: 0.15 g, 0.32 mmol) in DCM (10 mL) was added a solution of HCl in EtOAc (10 mL, 3.5 M). The mixture was stirred at room temperature for 2 h, then concentrated in vacuo. The residue was diluted with DCM (20 mL) and saturated Na2CO3 solution (20 mL). The organic layer was separated and the aqueous layer was extracted with a mixture of DCM and MeOH (10/1 (v/v), 20 mL×5). The combined organic layers was washed with brine (30 mL), dried over anhydrous Na2SO4, then filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/2N NH3 in MeOH (v/v)=5/1) to afford 3.10 A as a brown solid (0.10 g, 84%).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with DCM (20 mL) and saturated Na2CO3 solution (20 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with a mixture of DCM and MeOH (10/1 (v/v), 20 mL×5)
  5. washThe combined organic layers was washed with brine (30 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography (DCM/2N NH3 in MeOH (v/v)=5/1)

Sources & evidence

ORD record
ord-24e597f33c904d7a95ca29f480aadfa6
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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