Acetic Acid → HCID 18174537, compound

HRID 427640Notes

Reaction equation

HRID 427640 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-ea418a41e34f420594f668a76ea31396
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

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