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

Reaction equation

HRID 1826959 reaction equation
[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

Participants

6

Reactant 4

HCID 527Propanal2×HCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydride2×HCID 221362787-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-ylamine

Product 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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-866c82ac534a4e29819c25b53130ea7d
Source dataset
uspto-grants-2006_05
Patent number
US07053103B2

Linked notes

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