Sodium hydride → HCID 86679166, compound

HRID 712741Notes

Reaction equation

HRID 712741 reaction equation
[CH2:1]1[CH2:8][NH:7][S:4](=[O:6])(=[O:5])[CH2:3][CH2:2]1.[H-].[Na+].[Br:11][C:12]1[CH:13]=[N:14][CH:15]=[C:16]([CH2:18]Br)[CH:17]=1>CN(C=O)C.CCOC(C)=O>[Br:11][C:12]1[CH:17]=[C:16]([CH2:18][N:7]2[CH2:8][CH2:1][CH2:2][CH2:3][S:4]2(=[O:6])=[O:5])[CH:15]=[N:14][CH:13]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 3035081,4-ButanesultamHCID 149329483-Bromo-5-(bromomethyl)pyridine

Product 1

HCID 86679166HCID 86679166, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a vial is added 1,4-butanesultam (81 mg, 0.60 mmol) in 2 ml of DMF, followed by the addition of 60% NaH (24 mg, 0.6 mmol) at 0° C. The reaction mixture is stirred for 15 minutes, followed by the addition of To a vial is added 3-bromo-5-bromomethyl-pyridine, Intermediate E (100 mg, 0.40 mmol). The reaction mixture is stirred at room temperature for 2 hours. The reaction mixture is diluted with EtOAc, washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated to give the crude product. Purification by the flash column chromatography affords 86 mg of 2-(5-bromo-pyridin-3-ylmethyl)-[1,2]thiazinane 1,1-dioxide.

Workup

  1. additionfollowed by the addition of To
  2. stirringThe reaction mixture is stirred at room temperature for 2 hours
  3. washwashed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product
  8. customPurification by the flash column chromatography

Sources & evidence

ORD record
ord-825590ea050d48b2996bd1879f31bad0
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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