Toluene → 3-[5-amino-4-(3-formylbenzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methylbenzamide

HRID 251336Notes

Reaction equation

HRID 251336 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:16]=[CH:17][C:18]=2[CH3:19])[C:10]([NH:12][CH:13]2[CH2:15][CH2:14]2)=[O:11])[N:5]=[CH:4][C:3]=1[C:20](=[O:32])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]2OCC[O:28]2)[CH:22]=1.C1(C)C=CC=CC=1.CCOC(C)=O>CC(O)=O>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:16]=[CH:17][C:18]=2[CH3:19])[C:10]([NH:12][CH:13]2[CH2:15][CH2:14]2)=[O:11])[N:5]=[CH:4][C:3]=1[C:20](=[O:32])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]=[O:28])[CH:22]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 113963403-[5-amino-4-(3-[1,3]dioxolan-2-yl-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methyl-benzamide

Product 1

HCID 112806793-[5-amino-4-(3-formylbenzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methylbenzamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A mixture of 3-[5-amino-4-(3-[1,3]dioxolan-2-yl-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methyl-benzamide 5 (Example 8, 1.14 g, 2.6 mmol) was suspended in aqueous AcOH (10 mL, 1.5 M in H2O). Glacial AcOH was added dropwise until a clear solution was obtained. The reaction mixture was stirred at room temperature overnight. Evaporation of the solvent under reduced pressure to give a residue. Toluene and EtOAc were added and the mixture was concentrated again to give the crude product that could be purified by silica gel chromatography (hexanes/EtOAc: 1/4). The desired 3-[5-amino-4-(3-formyl-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methyl-benzamide 6 was obtained as a yellow foamy solid (0.91 g, 89%). MS m/z 389.1 [M+H]+; 1H NMR (300 MHz, CDCl3) δ0.61 (m, 2 H), 0.85 (dd, J1=6.9 Hz, J2=12.4 Hz, 2 H), 2.25 (s, 3 H), 2.87 (m, 1 H), 5.95 (brs, 2 H), 6.57 (brs, 1 H), 7.44 (d, J=8.0 Hz, 1 H), 7.67-7.78 (m, 4 H), 8.07 (s, 1 H), 8.09 (d, J=1.3 Hz, 1 H), 8.31 (s, 1H), 10.12 (s, 1 H) ppm.

Workup

  1. customwas obtained
  2. customEvaporation of the solvent under reduced pressure
  3. customto give a residue
  4. concentrationthe mixture was concentrated again
  5. customto give the crude product that
  6. customcould be purified by silica gel chromatography (hexanes/EtOAc: 1/4)

Sources & evidence

ORD record
ord-184b9a3655544549a8f6a24c8ef2462d
Source dataset
uspto-grants-2011_01
Patent number
US07863314B2

Reaction notes

Loading…