Triethylamine → Methyl 1-(3-chloropyridin-2-yl)-3-{[(methylsulfonyl)oxy]methyl}-1H-pyrazole-5-carboxylate

HRID 2044027Notes

Reaction equation

[Cl:1][C:2]1[C:3]([N:8]2[C:12](O)([C:13]([O:15][CH3:16])=[O:14])[CH2:11][C:10]([CH2:18][OH:19])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[S:27](Cl)([CH3:30])(=[O:29])=[O:28]>C1COCC1.O>[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]([CH2:18][O:19][S:27]([CH3:30])(=[O:29])=[O:28])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl 1-(3-chloropyridin-2-yl)-5-hydroxy-3-(hydroxymethyl)-4,5-dihydro-1H-pyrazole-5-carboxylate (28.5 g, 0.1 mol) and 15 g of triethylamine were introduced as initial charge in 150 ml of THF and the solution was cooled to 5° C. (11.4 g, 0.1 mol) of mesyl chloride were added at 0-5° C. within 20 min and the mixture was after-stirred at 0° C. for 2 hours. The reaction mixture was diluted with water and the product was extracted with ethyl acetate. The ethyl acetate solution was washed, dried and concentrated by evaporation. The viscous residue (product weight 31 g) contained, according to LC/MS, 98% of the product.

Workup

additionwere added at 0-5° C. within 20 min
extractionthe product was extracted with ethyl acetate
washThe ethyl acetate solution was washed
customdried
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-391e98263ac74a89ae87a90393498249
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586753B2

Reaction notes

Loading…