4-(5-Methyl-2-phenyl-oxazol-4-ylmethoxy)-benzenesulfonyl chloride → N-(4-benzoyl-1-ethyl-1H-pyrazol-3-yl)-4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzenesulfonamide

HRID 494370Notes

Reaction equation

HRID 494370 reaction equation
[NH2:1][C:2]1[C:6]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:8])=[CH:5][N:4]([CH2:15][CH3:16])[N:3]=1.[CH3:17][C:18]1[O:22][C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:20][C:19]=1[CH2:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1>N1C=CC=CC=1>[C:7]([C:6]1[C:2]([NH:1][S:37]([C:34]2[CH:35]=[CH:36][C:31]([O:30][CH2:29][C:19]3[N:20]=[C:21]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[O:22][C:18]=3[CH3:17])=[CH:32][CH:33]=2)(=[O:38])=[O:39])=[N:3][N:4]([CH2:15][CH3:16])[CH:5]=1)(=[O:8])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 210906794-(5-Methyl-2-phenyl-oxazol-4-ylmethoxy)-benzenesulfonyl chlorideHCID 68866724(3-amino-1-ethyl-1H-pyrazol-4-yl)-phenyl-methanone

Product 1

HCID 11272705N-(4-benzoyl-1-ethyl-1H-pyrazol-3-yl)-4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of the title A compound, (3-amino-1-ethyl-1H-pyrazol-4-yl)-phenyl-methanone (0.035 g, 0.16 mmol) in pyridine at RT, is added 4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzenesulfonyl chloride (0.06 g, 0.16 mmol) in pyridine. The solution is stirred at RT for 16 h. The reaction mixture is concentrated, the residue is taken up into ethyl acetate, washed with 1 N HCl, water, saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, filtered and concentrated at reduced pressure. The crude product is chromatographed on silica gel using 50% ethyl acetate in hexanes to yield N-(4-benzoyl-1-ethyl-1H-pyrazol-3-yl)-4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzenesulfonamide as a solid: MS [m/z] 541.1 [M-1]−.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. washwashed with 1 N HCl, water, saturated sodium bicarbonate and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated at reduced pressure
  6. customThe crude product is chromatographed on silica gel using 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-3db254b39d2c49c494b4b5df75605fc6
Source dataset
uspto-grants-2009_05
Patent number
US07538135B2

Reaction notes

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