Water → 2-(5-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrol-2-yl)-5-methyl-1,3,4-oxadiazole

HRID 909464Notes

Reaction equation

HRID 909464 reaction equation
[C:1]([NH:4][NH:5][C:6]([C:8]1[NH:9][C:10]([C:13]2[CH:18]=[C:17]([O:19][C:20]3[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=3)[CH:16]=[C:15]([O:30][C@@H:31]([CH3:35])[CH2:32][O:33][CH3:34])[CH:14]=2)=[CH:11][CH:12]=1)=O)(=[O:3])[CH3:2].C(N(CC)CC)C.O.C(OCC)(=O)C>C(#N)C>[CH3:34][O:33][CH2:32][C@H:31]([CH3:35])[O:30][C:15]1[CH:14]=[C:13]([C:10]2[NH:9][C:8]([C:6]3[O:3][C:1]([CH3:2])=[N:4][N:5]=3)=[CH:12][CH:11]=2)[CH:18]=[C:17]([O:19][C:20]2[CH:21]=[CH:22][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:24][CH:25]=2)[CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 66682299N'-Acetyl-5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrole-2-carbohydrazide

Product 1

HCID 1359774412-(5-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrol-2-yl)-5-methyl-1,3,4-oxadiazoleYield 59%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N′-Acetyl-5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrole-2-carbohydrazide (86.5 mg, 0.172 mmol) synthesized in Example (22a) was dissolved in acetonitrile (5 mL), (methoxycarbonysulfamoyl)triethylammonium hydroxide (60.7 mg, 0.258 mmol) and triethylamine (36 μL, 0.26 mmol) were added, and stirring was carried out at 80° C. for 3 hours under nitrogen atmosphere. The reaction solution was cooled to room temperature, water (20 mL) was added to the reaction solution, and extraction was carried out with ethyl acetate (30 mL). The organic layer was washed with saturated brine, and subsequently dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=50%-75%) to afford the desired compound (49.1 mg, yield 59%) as a white solid.

Workup

  1. washThe organic layer was washed with saturated brine
  2. dry with materialsubsequently dried over sodium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe resulting residue was purified
  5. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=50%-75%)

Sources & evidence

ORD record
ord-2a6240cb090c4fc19784cc698d851c02
Source dataset
uspto-grants-2011_09
Patent number
US08017610B2

Reaction notes

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