Water → N,N-Bis(4-methoxybenzyl)-5-(3-[(1S)-2-methoxy-1-methylethoxy]-5-{5-[(5S)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}phenoxy)pyridine-2-sulfonamide

HRID 1964713Notes

Reaction equation

HRID 1964713 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)(=[O:10])=[O:9])=[N:6][CH:7]=1.[CH3:30][O:31][CH2:32][C@H:33]([CH3:53])[O:34][C:35]1[CH:36]=[C:37]([OH:52])[CH:38]=[C:39]([C:41]2[NH:42][C:43]([C:46]3[O:47][C@@H:48]([CH3:51])[CH2:49][N:50]=3)=[CH:44][CH:45]=2)[CH:40]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][N:11]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[S:8]([C:5]2[CH:4]=[CH:3][C:2]([O:52][C:37]3[CH:38]=[C:39]([C:41]4[NH:42][C:43]([C:46]5[O:47][C@@H:48]([CH3:51])[CH2:49][N:50]=5)=[CH:44][CH:45]=4)[CH:40]=[C:35]([O:34][C@@H:33]([CH3:53])[CH2:32][O:31][CH3:30])[CH:36]=3)=[CH:7][N:6]=2)(=[O:10])=[O:9])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 666811783-[(1S)-2-Methoxy-1-methylethoxy]-5-{5-[(5S)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}phenolHCID 666833875-Chloro-N,N-bis(4-methoxybenzyl)pyridine-2-sulfonamide

Product 1

HCID 66681273N,N-Bis(4-methoxybenzyl)-5-(3-[(1S)-2-methoxy-1-methylethoxy]-5-{5-[(5S)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}phenoxy)pyridine-2-sulfonamideYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

5-Chloro-N,N-bis(4-methoxybenzyl)pyridine-2-sulfonamide (288 mg, 0.67 mmol) synthesized in Example (120b) and 3-[(1S)-2-methoxy-1-methylethoxy]-5-{5-[(5S)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}phenol (220 mg, 0.67 mmol) synthesized in Example (116d) were dissolved in N,N-dimethylformamide (3 mL), and cesium carbonate (434 mg, 1.33 mmol) was added, followed by stirring at 100° C. for 1 hour under nitrogen atmosphere. The reaction solution was cooled to room temperature, water (20 mL) was added, and extraction was carried out twice with ethyl acetate (20 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: methanol/methylene chloride=0.5%-5%) to afford the desired compound (160 mg, yield 33%) as a white solid.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionextraction
  3. washThe organic layer was washed with saturated brine
  4. dry with materialsubsequently dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified
  7. washsilica gel column chromatography (elution solvent: methanol/methylene chloride=0.5%-5%)

Sources & evidence

ORD record
ord-c34336f0cad84ba5895b847231f7b418
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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