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

HRID 2113792Notes

Reaction equation

HRID 2113792 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 7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-ylamine (5-45; 55 mg) 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 diluted with dichloromethane and washed with dilute aqueous sodium hydroxide. The organic phase was dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel eluting with an acetone/hexane gradient to provide a solid which was recrystallized from hexane to afford 17 mg of 5-5: mp 90-91° C.

Workup

  1. customthe reaction to completion
  2. washwashed with dilute aqueous sodium hydroxide
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. customevaporated
  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-a54ecf43febd4618b275ac5cc90ddced
Source dataset
uspto-grants-2008_10
Patent number
US07432283B2

Reaction notes

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