Water → HCID 24755126, compound

HRID 268643Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH:13]=[O:14])=[C:11]([CH:15]([CH3:17])[CH3:16])[C:10]([C:18]([OH:20])=O)=[N:9]2)=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.O.[CH3:43][NH:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[CH3:52]>C(Cl)Cl>[CH3:43][N:44]([CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[CH3:52])[C:18]([C:10]1[C:11]([CH:15]([CH3:16])[CH3:17])=[C:12]([CH:13]=[O:14])[N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[N:9]=1)=[O:20]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 1-(4-fluoro-phenyl)-5-formyl-4-isopropyl-1H-pyrazole-3-carboxylic acid (1.50 g, 5.43 mmol) in CH2Cl2 (100 mL) at 25° C. was added EDCI (1.56 g, 8.14 mmol) followed by HOBt.H2O (1.25 g, 8.14 mmol) and the reaction was stirred for 10 min at 25° C. Subsequently, methyl-(2-methyl-benzyl)-amine (1.10 g, 8.14 mmol) was added and the reaction was stirred for an additional 6 hrs at 25° C. The organic layer was then washed with HCl, saturated NaHCO3 and brine. After drying over Na2SO4 and concentration, the product was purified by column chromatography (10-25 % EtOAc/Hex) to afford desired 1-(4-fluoro-phenyl)-5-formyl-4-isopropyl-1H-pyrazole-3-carboxylic acid methyl-(2-methyl-benzyl)-amide as an oil (1.53 g, 71.6%). MS(APCI+) 394.2 m/z (M+H).

Workup

washThe organic layer was then washed with HCl, saturated NaHCO3 and brine
dry with materialAfter drying over Na2SO4 and concentration
customthe product was purified by column chromatography (10-25 % EtOAc/Hex)

Sources & evidence

ORD record: ord-71b0966a354245b89ba0f29834941af0
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446121B2

Reaction notes

Loading…