4-Heptanone → [7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl](1-propylbutyl)amine

HRID 916217

반응식

HRID 916217 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]1[CH2:15][CH2:14][CH2:13][C:12]2=[C:16]([NH2:20])[N:17]([CH3:19])[N:18]=[C:11]12.[CH3:21][CH2:22][CH2:23][C:24](=O)[CH2:25][CH2:26][CH3:27].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]1[CH2:15][CH2:14][CH2:13][C:12]2=[C:16]([NH:20][CH:24]([CH2:25][CH2:26][CH3:27])[CH2:23][CH2:22][CH3:21])[N:17]([CH3:19])[N:18]=[C:11]12

참가 물질

5

반응물 3

HCID 312464-Heptanone2회HCID 5049666Sodium triacetoxyborohydride2회HCID 221362787-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-ylamine

생성물 1

HCID 22136272[7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl](1-propylbutyl)amine

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

반응 조건

온도
60 °C

실험 절차

7-(2-Chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-ylamine (45.7 mg) and 4-heptanone (24 μL) were dissolved and stirred in 3 mL of dichloroethane. After 15 min, 44.5 mg of sodium triacetoxyborohydride was added. The reaction mixture was stirred at 60° C. during the day and at room temperature over night during 3 d. During this period, an additional 109 μL of 4-heptanone and an additional 104 mg of sodium triacetoxyborohydride were added to drive the reaction to completion. The reaction mixture was then partitioned between ethyl acetate and water. The ethyl acetate was dried with magnesium sulfate and concentrated. The crude product was chromatographed on silica gel eluting with an acetone/hexane gradient to provide 11 mg of [7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl](1-propyl butyl)amine as a crystalline film, ms m/z 389 (MH+).

후처리

  1. waitDuring this period
  2. customthe reaction to completion
  3. customThe reaction mixture was then partitioned between ethyl acetate and water
  4. dry with materialThe ethyl acetate was dried with magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product was chromatographed on silica gel eluting with an acetone/hexane gradient

출처 및 근거

ORD 기록
ord-0e5541c4d0494ec8a125cd1a6be59389
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07268146B2

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