Triethylamine → 2-(4-(5-(m-Tolyl)oxazole-4-carboxamido)-1H-pyrazol-1-yl)ethyl methanesulfonate

HRID 624064Notes

Reaction equation

HRID 624064 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.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl>[CH3:31][S:32]([O: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)(=[O:34])=[O:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68283198HCID 68283198, compound

Product 1

HCID 867042192-(4-(5-(m-Tolyl)oxazole-4-carboxamido)-1H-pyrazol-1-yl)ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 (178 mg, 0.57 mmol) in DCM (8 mL), Et3N (0.24 mL, 1.71 mmol) was added. After stirring for 5 min at 0° C., methanesulfonyl chloride (0.11 mL, 1.43 mmol) was added dropwise, and the resulting suspension was stirred at 0° C. for 1 h 15, then quenched with water and extracted with DCM (2×). The combined org. layers were washed with brine, dried (MgSO4) and concentrated in vacuo to obtain the title compound as an oil. LC-MS conditions A: tR=0.90 min, [M+H]+=391.03.

Workup

  1. additionwas added
  2. stirringthe resulting suspension was stirred at 0° C. for 1 h 15
  3. customquenched with water
  4. extractionextracted with DCM (2×)
  5. washlayers were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b11722ce31644caa88a06bfb6e94f340
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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