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

HRID 1483856노트

반응식

HRID 1483856 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 3776Isopropanol용매HCID 516892Sodium Bicarbonate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c089f007be924e35bc47003db6b89271
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09416132B2

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