Hydrochloric Acid → HCID 118390016, compound

HRID 1477988Notes

Reaction equation

HRID 1477988 reaction equation
[Cl:1][C:2]1[C:3]([NH:15][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]([NH:15][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 118390043HCID 118390043, compound

Product 1

HCID 118390016HCID 118390016, compoundYield 88.8%

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)amino)-2-azaspiro[4.5]decane-2-carboxylate (13.2B: 0.13 g, 0.28 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 1.5 h, then concentrated in vacuo. The residue was diluted with DCM (10 mL) and saturated Na2CO3 (10 mL) and then extracted with DCM/MeOH (v/v)=10/1 (30 mL×3). The combined organic layer was dried over anhydrous Na2SO4, 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 13.3B as a yellow solid (90 mg, 88%).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with DCM (10 mL) and saturated Na2CO3 (10 mL)
  3. extractionextracted with DCM/MeOH (v/v)=10/1 (30 mL×3)
  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-e78f673bb0a943c9bf35f67e6d3c6d97
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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