Sodium hydride → HCID 18519902, compound

HRID 1368576Notes

Reaction equation

HRID 1368576 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[N:19]([CH3:20])[N:18]=[C:17]([O:21][CH2:22][CH2:23][OH:24])[C:16]=2[C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:34][O:35][C:36]1[CH:37]=[N:38][C:39](S(C)(=O)=O)=[N:40][CH:41]=1>O1CCCC1.CC(N(C)C)=O.O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:15]2[N:19]([CH3:20])[N:18]=[C:17]([O:21][CH2:22][CH2:23][O:24][C:39]3[N:40]=[CH:41][C:36]([O:35][CH3:34])=[CH:37][N:38]=3)[C:16]=2[C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)(=[O:12])=[O:13])=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 41591512-Methanesulfonyl-5-methoxy-pyrimidineHCID 222820434-(tert-butyl)-N-[3-(2-hydroxyethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamide

Product 1

HCID 18519902HCID 18519902, compoundYield 61.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Procedure

To 4-(tert-butyl)-N-[3-(2-hydroxyethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamide (Example 2) (250 mg) in tetrahydrofuran (20 ml) at room temperature under an atmosphere of nitrogen was added sodium hydride (60% dispersion in oil, 47 mg) and the mixture was stirred for 5 minutes. To the mixture was added a solution of 5-methoxy-2-methylsulphonylpyrimidine (Aktual. Probl. Razvit. Nauchn. Issled. Molodykh Uch. Spets. Vil'nyus. Gosuniv. im. V. Kapsukasa, Mater. Konf. Molodykh Uch. Spets. Estestv. Khim. Fak. (1980), 87-90. Editor(s): Grigonis, I. Publisher: Vil'nyus. Gos. Univ. im. V. Kapsukasa, Vilnius, USSR.) (160 mg) in dimethylacetamide (2 ml) and the reaction was stirred for a further 16 hrs. The reaction was diluted with water (100 ml) and extracted with ethyl acetate (100 ml). The organic fraction was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica (10 g) eluted with dichloromethane: ether:hexane (10:2.5:1) to yield the title compound as a white solid (190 mg).

Workup

  1. stirringthe reaction was stirred for a further 16 hrs
  2. extractionextracted with ethyl acetate (100 ml)
  3. dry with materialThe organic fraction was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica (10 g)
  7. washeluted with dichloromethane: ether:hexane (10:2.5:1)

Sources & evidence

ORD record
ord-d715c5c9424c4547900d12d0642454dd
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

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