Triethylamine → Methanesulfonic acid pyrazolo[1,5-a]pyridin-2-ylmethyl ester

HRID 537898Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[N:6]1[N:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]2=[CH:8][C:7]=1[CH2:15][OH:16].C(N(CC)CC)C>ClCCl>[N:6]1[N:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]2=[CH:8][C:7]=1[CH2:15][O:16][S:2]([CH3:1])(=[O:4])=[O:3]

Participants

Conditions

Temperature: -10 °C

Procedure

A solution of methanesulfonyl chloride (0.149 g, 0.13 mmol) in dichloromethane (2 mL) was added to a solution of pyrazolo[1,5-a]pyridin-2-yl-methanol (0.148 g, 0.1 mmol) and triethylamine (0.303 g, 0.3 mmol) in dichloromethane (3 mL) at −10° C. under N2. After the addition was complete, the mixture was stirred at −10° C. for 1 h. Ice water (10 mL) was added, and the organic layer was separated, dried over sodium sulfate, filtered and concentrated under vacuum to give methanesulfonic acid pyrazolo[1,5-a]pyridin-2-ylmethyl ester as a yellow oil, which was used for the next step without further purification. A solution of this material (0.22 g, 0.1 mmol) in dry dichloromethane (2 mL) was added to a solution of 1-methyl-4-phenyl-1,3-dihydro-imidazole-2-thione (0.190 g, 0.1 mmol) and DIPEA (0.303 g, 0.3 mmol) in dry DMF (3 mL) at −10° C. under N2. The mixture was stirred at 0° C. for 2 hours, and was then concentrated under reduced pressure. The residue was purified by preparative HPLC to afford the title compound (50 mg, 15%). LC-MS: m/z=321.1 (MH+), tR=2.16 min, method F.

Workup

additionAfter the addition
customthe organic layer was separated
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-5b218a4d91824e64b0297fa1f351d285
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865711B2

Reaction notes

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