Sodium hydride → HCID 22322122, compound

HRID 2300254Notes

Reaction equation

HRID 2300254 reaction equation
[H-].[Na+].[CH3:3][N:4]([S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.ClC1[C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:28][N:27]=[C:26]2[S:35][N:36]=[C:37]([CH3:38])[C:25]=12>CN1CCCC1=O>[CH3:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([S:12]([N:4]([CH2:5][C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)[C:3]2[C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:28][N:27]=[C:26]3[S:35][N:36]=[C:37]([CH3:38])[C:25]=23)(=[O:14])=[O:13])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3755104HCID 3755104, compoundHCID 14809185HCID 14809185, compound

Product 1

HCID 22322122HCID 22322122, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a stirred mixture of 0.366 g (8.4 mmol) of sodium hydride (60% in oil) in 10 ml of dry 1-methyl-2-pyrrolidinone was added (portionwise) 2.34 g (8.4 mmol) of methyl (4-methoxybenzenesulfonyl)pyridin-3-ylmethyl-amine. The mixture was stirred at room temperature until gas evolution ceased and 1.80 g of (7.0 mmol) of ethyl 4-chloro-3-methylisothiazolo[5,4-b]pyridine-5-carboxylate added. The mixture was heated at 80-90° C. for 44 hours, the solvent removed under vacuum and the residue diluted with water. The mixture was extracted with ethyl acetate and the extract washed with 2N citric acid, H2O, 1 N NaHCO3, brine and dried (Na2SO4). The solution was filtered through a thin pad of hydrous magnesium silicate and the pad washed with ethyl acetate. The filtrate was concentrated to dryness to give 2.39 g of ethyl 4-[(4-methoxybenzenesulfonyl)-pyridin-3-ylmethylamino]-3-methylisothiazolo[5,4-b]pyridine-5-carboxylate as a yellow solid, m.p. 142-144° C.

Workup

  1. temperatureThe mixture was heated at 80-90° C. for 44 hours
  2. customthe solvent removed under vacuum
  3. additionthe residue diluted with water
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe extract washed with 2N citric acid, H2O, 1 N NaHCO3, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationThe solution was filtered through a thin pad of hydrous magnesium silicate
  8. washthe pad washed with ethyl acetate
  9. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-a972c9ae4969459184f15c5f1f5d1f50
Source dataset
uspto-grants-2002_12
Patent number
US06498167B2

Reaction notes

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