4-Toluenesulfonyl chloride → 2-(4-(5-(m-Tolyl)oxazole-4-carboxamido)-1H-pyrazol-1-yl)ethyl 4-methyl-benzenesulfonate

HRID 624065Notes

Reaction equation

[OH:1][CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([NH:9][C:10]([C:12]2[N:13]=[CH:14][O:15][C:16]=2[C:17]2[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=2)=[O:11])[CH:6]=[N:5]1.CCN(CC)CC.[C:31]1([CH3:41])[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1>C(Cl)Cl>[CH3:41][C:31]1[CH:36]=[CH:35][C:34]([S:37]([O:1][CH2:2][CH2:3][N:4]2[CH:8]=[C:7]([NH:9][C:10]([C:12]3[N:13]=[CH:14][O:15][C:16]=3[C:17]3[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=3)=[O:11])[CH:6]=[N:5]2)(=[O:39])=[O:38])=[CH:33][CH:32]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To an ice-cooled solution of N-(1-(2-hydroxyethyl)-1H-pyrazol-4-yl)-5-(m-tolyl)oxazole-4-carboxamide (2.57 g, 8.23 mmol) in DCM (70 mL), Et3N (3.44 mL, 24.69 mmol) was added. After stirring for 20 min at 0° C., p-toluenesulfonyl chloride (1.73 g, 9.05 mmol), was added dropwise, and the resulting suspension was stirred at 0° C. for 3 h, then quenched with water and extracted with DCM (2×). The combined org. layers were washed with 1 N aq. HCl-solution and brine, dried (MgSO4), filtered and concentrated in vacuo to obtain the title compound as an oil. LC-MS conditions A: tR=0.93 min, [M+H]+=467.46.

Workup

additionwas added
stirringthe resulting suspension was stirred at 0° C. for 3 h
customquenched with water
extractionextracted with DCM (2×)
washlayers were washed with 1 N aq. HCl-solution and brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-91b0d8560dcd482fbd4728079f9127b7
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303023B2

Reaction notes

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