Sodium hydride → HCID 25128162, compound

HRID 389307Notes

Reaction equation

HRID 389307 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[C:6]([CH3:27])=[CH:7][C:8]([CH2:14][C:15]2[C:16]([CH3:26])=[N:17][N:18]([CH2:21][CH2:22][C:23]([NH2:25])=[O:24])[C:19]=2[CH3:20])=[C:9]2[C:13]=1[CH2:12][CH2:11][CH2:10]2.[CH:28]([S:31](Cl)(=[O:33])=[O:32])([CH3:30])[CH3:29]>O1CCCC1>[CH3:3][O:4][C:5]1[C:6]([CH3:27])=[CH:7][C:8]([CH2:14][C:15]2[C:16]([CH3:26])=[N:17][N:18]([CH2:21][CH2:22][C:23]([NH:25][S:31]([CH:28]([CH3:30])[CH3:29])(=[O:33])=[O:32])=[O:24])[C:19]=2[CH3:20])=[C:9]2[C:13]=1[CH2:12][CH2:11][CH2:10]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 824082-Propanesulfonyl chlorideHCID 66812534HCID 66812534, compound

Product 1

HCID 25128162HCID 25128162, compoundYield 12.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To the suspension of 60% Sodium hydride (76 mg, 0.0019 mole) in Tetrahydrofuran (2 ml), the solution of 3-[4-(7-Methoxy-6-methyl-indan-4-ylmethyl)-3,5-dimethyl-pyrazol-1-yl]-propionamide (500 mg, 0.00146 mole) in Tetrahydrofuran (5 ml) was added at room temperature and stirred for 20 minutes. A solution of Isopropyl sulfonyl chloride (0.18 ml, 0.0016 moles) in Tetrahydrofuran (3 ml) was added at 0-5° C. and stirred at 15-25° C. for 3 hours. Tetrahydrofuran was distilled under vacuum, dilute hydrochloric acid (20 ml) was added to the reaction mixture and extracted with Ethyl Acetate (50 ml). The Ethyl acetate layer was dried over Sodium sulphate and distilled under vacuum to give a crude product which was purified by column chromatography using Ethylacetate as a mobile phase. The fractions were distilled to give 80 mg of desired compound as a solid.

Workup

  1. stirringstirred at 15-25° C. for 3 hours
  2. distillationTetrahydrofuran was distilled under vacuum, dilute hydrochloric acid (20 ml)
  3. additionwas added to the reaction mixture
  4. extractionextracted with Ethyl Acetate (50 ml)
  5. dry with materialThe Ethyl acetate layer was dried over Sodium sulphate
  6. distillationdistilled under vacuum
  7. customto give a crude product which
  8. customwas purified by column chromatography
  9. distillationThe fractions were distilled

Sources & evidence

ORD record
ord-618c7d5c975f46ba96970b6ab1316eda
Source dataset
uspto-grants-2013_02
Patent number
US08378118B2

Reaction notes

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