Triethylamine → methanesulfonic acid 2-(3,5-diethyl-1-methanesulfonyl-1H-pyrazol-4-yl)-ethyl ester

HRID 1802786Notes

Reaction equation

HRID 1802786 reaction equation
[CH2:1]([C:3]1[C:7]([CH2:8][CH2:9][OH:10])=[C:6]([CH2:11][CH3:12])[NH:5][N:4]=1)[CH3:2].[CH3:13][S:14](Cl)(=[O:16])=[O:15].C(N(CC)CC)C>C(Cl)Cl>[CH2:11]([C:6]1[C:7]([CH2:8][CH2:9][O:10][S:14]([CH3:13])(=[O:16])=[O:15])=[C:3]([CH2:1][CH3:2])[N:4]([S:14]([CH3:13])(=[O:16])=[O:15])[N:5]=1)[CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 578992212-(3,5-diethyl-1H-pyrazol-4-yl)-ethanol

Product 1

HCID 57899261methanesulfonic acid 2-(3,5-diethyl-1-methanesulfonyl-1H-pyrazol-4-yl)-ethyl esterYield 60.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3,5-diethyl-1H-pyrazol-4-yl)-ethanol (0.8 g, 4.8 mmol) in methylene chloride (20 mL) was added methanesulfonyl chloride (0.92 mL, 12 mmol) and triethylamine (2.0 mL, 14 mmol). The mixture was stirred at room temperature for 16 h and was loaded directly on to a silica gel column and eluted (methylene chloride/heptane followed by ethyl acetate/methylene chloride) to provide methanesulfonic acid 2-(3,5-diethyl-1-methanesulfonyl-1H-pyrazol-4-yl)-ethyl ester (940 mg, 41% yield).

Workup

  1. washeluted (methylene chloride/heptane followed by ethyl acetate/methylene chloride)

Sources & evidence

ORD record
ord-262b4ec1efc34ea78adeb4da51db90ed
Source dataset
uspto-grants-2013_01
Patent number
US08349883B2

Reaction notes

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