Water → HCID 22244641, compound

HRID 891125Notes

Reaction equation

[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=2)[C:10]([O:12][CH3:13])=[O:11])=[C:5]([CH3:17])[N:4]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25]OS(C)(=O)=O)=[CH:20][CH:19]=2)[N:3]=1.[N-:31]=[N+:32]=[N-:33].[Na+].O>CN(C)C=O>[N:31]([CH2:25][CH2:24][C:21]1[CH:22]=[CH:23][C:18]([N:4]2[C:5]([CH3:17])=[C:6]([C:7]3[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=3)[C:10]([O:12][CH3:13])=[O:11])[C:2]([CH3:1])=[N:3]2)=[CH:19][CH:20]=1)=[N+:32]=[N-:33]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of methyl 3-[3,5-dimethyl-1-(4-{2-[(methylsulfonyl)oxy]ethyl}phenyl)-1H-pyrazol-4-yl]benzoate (step 2, 2.0 mmol) and KI (330 mg, 2.0 mmol) in N,N-dimethylformamide (10 mL) was added sodium azide (260 mg, 4.0 mmol), and then the resulting mixture was stirred for 1.5 h at 100° C. The reaction mixture was poured into water (100 mL), and extracted with ethyl acetate/toluene (4:1). The organic layer was washed with water (50 mL) and brine (50 mL), then dried (Na2SO4). After removal of the solvent, the crude product was purified by TLC with hexane/ethyl acetate (1:1) to give the title compound as yellow oil (quant.): 1H-NMR (CDCl3) δ 8.01 (2H, s), 7.53-7.34 (6H, m), 3.95 (3H, s), 3.55 (2H, t, J=7.1 Hz), 2.96 (2H, t, J=7.1 Hz), 2.33 (3H, s), 2.30 (3H, s).

Workup

extractionextracted with ethyl acetate/toluene (4:1)
washThe organic layer was washed with water (50 mL) and brine (50 mL)
dry with materialdried (Na2SO4)
customAfter removal of the solvent
customthe crude product was purified by TLC with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record: ord-8ddf50f8f9f84125ac4b00fb5b9f0db7
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07001917B2

Reaction notes

Loading…