Diisopropylethylamine → 4-((3-(3-Chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)amino)cyclohexanone

HRID 1483857노트

반응식

HRID 1483857 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.[NH2:18][CH:19]1[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]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]([NH:18][CH:19]4[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]4)=[N:3][C:4]=23)[CH:16]=[CH:15][CH:14]=1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 99123064-AminocyclohexanoneHCID 596622385-Chloro-3-(3-chloro-phenyl)-pyrazolo[1,5-a]pyrimidine

생성물 1

HCID 712276764-((3-(3-Chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)amino)cyclohexanone수율 24%

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), 4-aminocyclohexanone (43 mg, 0.379 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 4-((3-(3-chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)amino)cyclohexanone (30 mg, 24% 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-ff6934fe1d084306b90b6ee2335a8a89
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09416132B2

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