tert-butyl (3R)-3-aminopiperidine-1-carboxylate → HCID 86691786, compound

HRID 1500768Notes

Reaction equation

HRID 1500768 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:9]=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)[N:3]=1.[NH2:17][C@@H:18]1[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]1>C(O)C>[N:10]1[N:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]2=[C:8]([C:4]2[N:3]=[C:2]([NH:17][C@@H:18]3[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]3)[CH:7]=[CH:6][N:5]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 1501974tert-butyl (3R)-3-aminopiperidine-1-carboxylateHCID 86691787HCID 86691787, compound

Product 1

HCID 86691786HCID 86691786, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-(4-chloropyrimidin-2-yl)pyrazolo[1,5-a]pyridine (Preparation 33, 130 mg, 0.56 mmol) and (R)-tert-butyl 3-aminopiperidine-1-carboxylate (326 mg, 1.63 mmol) in ethanol (5 mL) was heated overnight at 100° C. After cooling to ambient temperature, the solvent was evaporated under reduced pressure and the residue was taken up in a mixture of chloroform and water. The aqueous layer was separated and washed with chloroform (×2). The combined organic extracts were dried (MgSO4) and evaporated in vacuo. The crude product was purified by flash chromatography (dichloromethane to 95:5 dichloromethane/methanol) to give the title compound (150 mg, 68%).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionthe residue was taken up in a mixture of chloroform and water
  3. customThe aqueous layer was separated
  4. washwashed with chloroform (×2)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. customevaporated in vacuo
  7. customThe crude product was purified by flash chromatography (dichloromethane to 95:5 dichloromethane/methanol)

Sources & evidence

ORD record
ord-952a0f7d3a2f4d72933ab6c2553550aa
Source dataset
uspto-grants-2015_12
Patent number
US09206183B2

Reaction notes

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