Diisopropylethylamine → (S)-1-(3-(3-chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidin-3-amine

HRID 1483856Notes

Reaction equation

HRID 1483856 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=3)=[C:4]2[N:3]=1.[NH:18]1[CH2:23][CH2:22][CH2:21][C@H:20]([NH2:24])[CH2:19]1.CCN(C(C)C)C(C)C>CC(O)C.C([O-])(O)=O.[Na+]>[Cl:17][C:13]1[CH:12]=[C:11]([C:10]2[CH:9]=[N:8][N:5]3[CH:6]=[CH:7][C:2]([N:18]4[CH2:23][CH2:22][CH2:21][C@H:20]([NH2:24])[CH2:19]4)=[N:3][C:4]=23)[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 855017(S)-piperidin-3-amineHCID 596622385-Chloro-3-(3-chloro-phenyl)-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 71227735(S)-1-(3-(3-chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidin-3-amineYield 28.2%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 5-chloro-3-(3-chlorophenyl)pyrazolo[1,5-a]pyrimidine (100 mg, 0.379 mmol), (S)-piperidin-3-amine (76 mg, 0.757 mmol), and DIEA (0.158 ml, 1.515 mmol) in 2-propanol (3 ml) was irradiated to 150° C. for 14 h in a Biotage microwave. After cooling, the mixture was diluted with saturated aqueous NaHCO3, and extracted three times with EtOAc. The combined extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo. After absorbing on celite, the compound was purified by chromatography (12 g silica, 0-15% methanol/DCM) to give (S)-1-(3-(3-chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidin-3-amine (35 mg, 28% yield) as a white solid.

Workup

  1. customwas irradiated to 150° C. for 14 h in a Biotage microwave
  2. temperatureAfter cooling
  3. extractionextracted three times with EtOAc
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customAfter absorbing on celite
  8. customthe compound was purified by chromatography (12 g silica, 0-15% methanol/DCM)

Sources & evidence

ORD record
ord-c089f007be924e35bc47003db6b89271
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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