Hydrochloric Acid → HCID 118390008, compound

HRID 1477959Notes

Reaction equation

HRID 1477959 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 93.1%

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 B: 0.19 g, 0.40 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 (10 mL) and saturated Na2CO3 aqueous solution (10 mL) and then the mixture was extracted with DCM/MeOH (v/v)=10/1 (30 mL×5). The combined organic layer was 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 give 3.10 B as a light yellow solid (0.14 g, 93%).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with DCM (10 mL) and saturated Na2CO3 aqueous solution (10 mL)
  3. extractionthe mixture was extracted with DCM/MeOH (v/v)=10/1 (30 mL×5)
  4. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (DCM/2N NH3 in MeOH (v/v)=5/1)

Sources & evidence

ORD record
ord-f4240c414fdf453c83cd6c18632f3e2f
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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