Triethylamine → HCID 86663312, compound

HRID 2403222Notes

Reaction equation

HRID 2403222 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[F:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[C:14]1[N:18]=[C:17]([C:19]2[CH:20]=[N:21][N:22]([CH2:30][CH2:31][OH:32])[C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:16][N:15]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:4][S:1]([O:32][CH2:31][CH2:30][N:22]1[C:23]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[C:19]([C:17]2[O:16][N:15]=[C:14]([C:8]3[CH:9]=[C:10]([F:13])[CH:11]=[CH:12][C:7]=3[F:6])[N:18]=2)[CH:20]=[N:21]1)(=[O:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66795539HCID 66795539, compound

Product 1

HCID 86663312HCID 86663312, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Mesyl chloride (280 μL; 3.6 mmol) was added to a solution of 2-(4-(3-(2,5-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-phenyl-1H-pyrazol-1-yl)ethanol (663 mg; 1.8 mmol), obtained from step 1, and triethylamine (502 μL; 3.6 mmol) in dry DCM (5 mL) at 0° C. The tube was sealed and allowed to warm to room temperature overnight. The mixture was washed with saturated aqueous sodium hydrogen carbonate and the organic fraction passed through a hydrophobic frit and the solvent removed in vacuo to give the title compound as a pale yellow solid (785 mg; 97%). 1H NMR (CDCl3, 400 MHz) δ 8.31 (1 H, s), 7.69-7.64 (1 H, m), 7.59-7.81 (3 H, m), 7.50-7.45 (2H, m), 7.21-7.10 (2 H, m), 4.64 (2 H, t, J=5.2 Hz), 4.38 (2 H, t, J=5.2 Hz), 2.90 (3 H, s). LC/MS: 447 (M+H)+. HPLC (Method A) Rt=3.69 min (Purity: 99.4%).

Workup

  1. customThe tube was sealed
  2. washThe mixture was washed with saturated aqueous sodium hydrogen carbonate
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-dcf615b6bf054d4bb4d05b2e9e9eeedf
Source dataset
uspto-grants-2014_08
Patent number
US08802663B2

Reaction notes

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