Diisopropylethylamine → 3-[5-amino-4-(4-methyl-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methyl-benzamide

HRID 251341Notes

Reaction equation

HRID 251341 reaction equation
C(O[C:4](=O)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7](OCCN2CCOCC2)[CH:6]=1)C.[NH2:21][C:22]1[N:26]([C:27]2[CH:28]=[C:29]([CH:36]=[CH:37][C:38]=2[CH3:39])[C:30]([NH:32][CH:33]2[CH2:35][CH2:34]2)=[O:31])[N:25]=[CH:24][C:23]=1[C:40](=[O:49])C1C=CC=C(CO)C=1.C(N(C(C)C)CC)(C)C>C(O)C>[NH2:21][C:22]1[N:26]([C:27]2[CH:28]=[C:29]([CH:36]=[CH:37][C:38]=2[CH3:39])[C:30]([NH:32][CH:33]2[CH2:35][CH2:34]2)=[O:31])[N:25]=[CH:24][C:23]=1[C:40](=[O:49])[C:8]1[CH:9]=[CH:10][C:5]([CH3:4])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 114066393-[5-amino-4-(3-hydroxymethyl-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methyl-benzamideHCID 58089039Ethyl 3-{[2-(4-morpholinyl)ethyl]oxy}benzoate

Product 1

HCID 111647033-[5-amino-4-(4-methyl-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methyl-benzamideYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(4-methyl-benzoyl)-3-phenylamino-acrylonitrile 2 (205 mg, 0.78 mmol), N-cyclopropyl-3-hydrazino-4-methyl-benzamide trifluoroacetic acid salt 7 (Example 6C, 250 mg, 0.78 mmol) and diisopropylethylamine (0.14 mL, 0.78 mmol) in 8 mL of ethanol was heated at 650C in for 18 h. Solvent was removed and the residue was purified by silica gel column chromatography (EtOAc/hexanes, gradient from 1/3 to 3/1). The product can be further purified by trituration with Et2O to give 3-[5-amino-4-(4-methyl-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methyl-benzamide 3 as a white solid (64 mg, 22%). HPLC (4 minute gradient) tR 2.26 min;

Workup

  1. customSolvent was removed
  2. customthe residue was purified by silica gel column chromatography (EtOAc/hexanes, gradient from 1/3 to 3/1)
  3. customThe product can be further purified by trituration with Et2O

Sources & evidence

ORD record
ord-5fbc8dcb8f46416c83ec8328014cff08
Source dataset
uspto-grants-2011_01
Patent number
US07863314B2

Reaction notes

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