Acetic Acid → HCID 18174537, compound

HRID 395789Notes

Reaction equation

HRID 395789 reaction equation
[C:1]([NH:4][C:5]1[CH:21]=[CH:20][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[O:10])=[C:7]([NH:22][C:23]([CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[O:24])[CH:6]=1)(=[O:3])[CH3:2].[N:31]1[CH:36]=[CH:35][C:34]([CH:37]=O)=[CH:33][CH:32]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:1]([NH:4][C:5]1[CH:21]=[CH:20][C:8]([C:9]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)=[O:10])=[C:7]([NH:22][C:23]([CH:25]2[CH2:30][CH2:29][N:28]([CH2:37][C:34]3[CH:35]=[CH:36][N:31]=[CH:32][CH:33]=3)[CH2:27][CH2:26]2)=[O:24])[CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 133894-PyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 18174444HCID 18174444, compound

Product 1

HCID 18174537HCID 18174537, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred suspension of 4-acetylamino-N-(4-methoxyphenyl)-2-[(4-piperidinylcarbonyl)amino]benzamide (0.4 g, 0.97 mmol), 4-pyridinecarboxaldehyde (0.11 mL, 1.17 mmol) and acetic acid (0.085 mL, 1.46 mmol) in 1,2-dichloroethane (20 mL) was added sodium triacetoxyborohydride (0.31 g, 1.46 mmol). After stirring overnight, the white solid was filtered off and the filtrate was concentrated in vacuo. The residue was suspended in diethyl ether, sonicated, and filtered. The combined solids were then washed with water, filtered and dried in vacuo to give 0.37 g (76%) of the title compound as a white solid.

Workup

  1. filtrationthe white solid was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customsonicated
  4. filtrationfiltered
  5. washThe combined solids were then washed with water
  6. filtrationfiltered
  7. customdried in vacuo

Sources & evidence

ORD record
ord-c919d8b5639b40439dc68598cd259b51
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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