1-benzyl-5-methyl-1H-pyrazole-4-carboxylic acid → 1-Benzyl-N-[3-cyano-4-(4-morpholinopiperidin-1-yl)phenyl]-5-methylpyrazole-4-carboxamide

HRID 1744653Notes

Reaction equation

HRID 1744653 reaction equation
[CH2:1]([N:8]1[C:12]([CH3:13])=[C:11]([C:14]([OH:16])=O)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:17][C:18]1[CH:19]=[CH:20][C:21]([N:26]2[CH2:31][CH2:30][CH:29]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[CH2:28][CH2:27]2)=[C:22]([CH:25]=1)[C:23]#[N:24]>>[CH2:1]([N:8]1[C:12]([CH3:13])=[C:11]([C:14]([NH:17][C:18]2[CH:19]=[CH:20][C:21]([N:26]3[CH2:31][CH2:30][CH:29]([N:32]4[CH2:33][CH2:34][O:35][CH2:36][CH2:37]4)[CH2:28][CH2:27]3)=[C:22]([C:23]#[N:24])[CH:25]=2)=[O:16])[CH:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 64931761-benzyl-5-methyl-1H-pyrazole-4-carboxylic acidHCID 219423895-Amino-2-(4-morpholinopiperidin-1-yl)benzonitrile

Product 1

HCID 210183281-Benzyl-N-[3-cyano-4-(4-morpholinopiperidin-1-yl)phenyl]-5-methylpyrazole-4-carboxamideYield 22.9%

Procedure

The reaction and treatment in the same manner as in Example 64 were conducted using 1-benzyl-5-methylpyrazole-4-carboxylic acid (0.7 g) and 5-amino-2-(4-morpholinopiperidin-1-yl)benzonitrile (0.93 g) and the resulting product was recrystallized from a mixed solvent of ethyl acetate-diisopropyl ether to give the title compound (0.36 g), melting point: 155° C.

Workup

  1. customThe reaction and treatment in the same manner as in Example 64
  2. customthe resulting product was recrystallized from a mixed solvent of ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-52c5f5f42a4741099048862abb88f990
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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