Water → HCID 18676112, compound

HRID 1635506Notes

Reaction equation

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

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 2-chloro-4-[1-(3-methylphenyl)-3-methyl-1H-pyrazol-5-yl]pyridine (Example 45; 1.0 g, 0.0035 mol) and methanesulfonic acid sodium salt (3.24 g, 0.021 mol) in 15 mL of DMF was heated at 140° C. for 24 hours. After the mixture was cooled, water was added and the aqueous phase was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated and the crude was purified by chromatography on silica gel (ethyl acetate/hexane, 1:1) to give 0.45 g (40% yield) of product as a yellow solid: mp: 140-142° C.; Anal. Calc'd. for C17H17N3SO2: C, 62.36; H, 5.23; N, 12.83; S, 9.79. Found: C, 62.16; H, 5.31; N, 12.74; S, 9.86.

Workup

temperatureAfter the mixture was cooled
extractionthe aqueous phase was extracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated
customthe crude was purified by chromatography on silica gel (ethyl acetate/hexane, 1:1)

Sources & evidence

ORD record: ord-156bfdc6090c41ef94b00027b80eb7c8
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06509361B1

Reaction notes

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