Propanal → [7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl]dipropylamine

HRID 1826959

반응식

HRID 1826959 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.[CH:21](=O)[CH2:22][CH3:23].C(O[BH-](O[C:35](=O)[CH3:36])OC(=O)C)(=O)C.[Na+].Cl[CH:40](Cl)C>ClCCl>[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]([N:20]([CH2:40][CH2:35][CH3:36])[CH2:21][CH2:22][CH3:23])[N:17]([CH3:19])[N:18]=[C:11]12

참가 물질

6

반응물 4

HCID 527Propanal2회HCID 63651,1-DichloroethaneHCID 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 10126373[7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl]dipropylamine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 55 mg of 7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-ylamine in 3 mL of dichloroethane was added 29 μL of propionaldehyde followed a few minutes later by 124 mg of sodium triacetoxyborohydride. The reaction mixture was stirred at room temperature for 2 d, during which time an additional 30 μL of propionaldehyde and an additional 62 mg of sodium triacetoxyborohydride were added to drive the reaction to completion. The mixture was then diluted with dichloromethane and washed with dilute aqueous sodium hydroxide. The organics were dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel eluting with an acetone/hexane gradient to provide a solid which was recrystallized from hexane to give 17 mg of [7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl]dipropylamine, mp 90–91° C.

후처리

  1. customthe reaction to completion
  2. washwashed with dilute aqueous sodium hydroxide
  3. dry with materialThe organics were dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel eluting with an acetone/hexane gradient
  6. customto provide a solid which
  7. customwas recrystallized from hexane

출처 및 근거

ORD 기록
ord-866c82ac534a4e29819c25b53130ea7d
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07053103B2

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