Sodium Chloride → Ethyl 7-methyl-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine-9-carboxylate 2,2-dioxide

HRID 1405643Notes

Reaction equation

HRID 1405643 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][C:5]([CH3:13])=[CH:4][N:3]=1.Cl[CH2:15][CH2:16][S:17](Cl)(=[O:19])=[O:18].C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Na+]>CN(C=O)C.O.N1C=CC=CC=1>[CH3:13][C:5]1[CH:6]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:2]2[N:3]([CH:4]=1)[CH2:15][CH2:16][S:17](=[O:19])(=[O:18])[N:1]=2

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 13070843Ethyl 2-amino-5-methylnicotinate

Product 1

HCID 66748581Ethyl 7-methyl-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine-9-carboxylate 2,2-dioxide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 2-amino-5-methylpyridine-3-carboxylate (368 mg) in DMF (20 mL) were added pyridine (0.66 mL) and 2-chloroethanesulfonyl chloride (0.32 mL), and the mixture was stirred at room temperature for 3 hr. To the reaction mixture were added water (50 mL) and sodium carbonate (1 g), sodium chloride was saturated and the mixture was extracted 3 times with ethyl acetate. The extracts were collected, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (111 mg) as a brown solid.

Workup

  1. extractionthe mixture was extracted 3 times with ethyl acetate
  2. customThe extracts were collected
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (methanol/ethyl acetate)

Sources & evidence

ORD record
ord-9e8405449272477a8395702ad746ba95
Source dataset
uspto-grants-2014_12
Patent number
US08916551B2

Reaction notes

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