Benzaldehyde → N4-[4-tert-Butyl-2-(1-benzylpiperidin-4-yloxy)benzoyl]-N3-(4-methoxybenzoyl)-3,4-pyridinediamine

HRID 1445446Notes

Reaction equation

HRID 1445446 reaction equation
[C:1]([C:5]1[CH:30]=[CH:29][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[NH:18][C:19](=[O:28])[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[O:10])=[C:7]([O:31][CH:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH:38](=O)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>>[C:1]([C:5]1[CH:30]=[CH:29][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[NH:18][C:19](=[O:28])[C:20]2[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)=[O:10])=[C:7]([O:31][CH:32]2[CH2:37][CH2:36][N:35]([CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH2:34][CH2:33]2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 240BenzaldehydeHCID 11576987N4-[4-tert-butyl-2-(piperidin-4-yloxy)benzoyl]-N3-(4-methoxybenzoyl)-3,4-pyridinediamine

Product 1

HCID 11721296N4-[4-tert-Butyl-2-(1-benzylpiperidin-4-yloxy)benzoyl]-N3-(4-methoxybenzoyl)-3,4-pyridinediamineYield 106%

Procedure

In a 4 mL screw cap vial, N4-[4-tert-butyl-2-(piperidin-4-yloxy)benzoyl]-N3-(4-methoxybenzoyl)-3,4-pyridinediamine (38 mg, 76 μmol) was dissolved in 1 mL of freshly prepared dry 95:5 MeOH:AcOH. Benzaldehyde (24.1 mg, 227 μmol, 3 eq) was added and the vial was capped. After 10 minutes, sodium cyanoborohydride solution (0.5 mL of a 19.0 mg/mL freshly prepared stock in dry 95:5 MeOH:AcOH, 9.51 mg NaCNBH3, 151 μmol, 2 eq) was then added to the solution. The vial was re-capped and shaken overnight at room temperature. The mixture was then purified using the method described in Example 34-B to provide the desired compound as a yellow solid (47.5 mg, 106%).

Workup

  1. customIn a 4 mL screw cap vial
  2. customof freshly prepared
  3. dry with materialdry 95:5 MeOH
  4. customthe vial was capped
  5. dry with materialsodium cyanoborohydride solution (0.5 mL of a 19.0 mg/mL freshly prepared stock in dry 95:5 MeOH
  6. additionAcOH, 9.51 mg NaCNBH3, 151 μmol, 2 eq) was then added to the solution
  7. customThe vial was re-capped
  8. customThe mixture was then purified

Sources & evidence

ORD record
ord-c182ae8b97294014959c3c580c115a74
Source dataset
uspto-grants-2010_02
Patent number
US07666866B2

Reaction notes

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