Ethanesulfonylchloride, 2-chloro- → 9-{[4-(1-Methylpropyl)phenoxy]methyl}-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

HRID 1405859Notes

Reaction equation

HRID 1405859 reaction equation
[H-].[Na+].Cl[CH2:4][CH2:5][S:6](Cl)(=[O:8])=[O:7].[CH3:10][CH:11]([C:14]1[CH:28]=[CH:27][C:17]([O:18][CH2:19][C:20]2[C:21]([NH2:26])=[N:22][CH:23]=[CH:24][CH:25]=2)=[CH:16][CH:15]=1)[CH2:12][CH3:13]>C1COCC1>[CH3:10][CH:11]([C:14]1[CH:28]=[CH:27][C:17]([O:18][CH2:19][C:20]2[C:21]3=[N:26][S:6](=[O:8])(=[O:7])[CH2:5][CH2:4][N:22]3[CH:23]=[CH:24][CH:25]=2)=[CH:16][CH:15]=1)[CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 667480763-{[4-(1-Methylpropyl)phenoxy]methyl}pyridin-2-amine

Product 1

HCID 667480109-{[4-(1-Methylpropyl)phenoxy]methyl}-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of NaH (60%, 117 mg) in THF (dry) (4 mL) was added 2-chloroethanesulfonyl chloride (0.185 mL) at 0° C. and the mixture was stirred for 10 min at the same temperature. A solution of 3-{[4-(1-methylpropyl)phenoxy]methyl}pyridin-2-amine (150 mg) in THF (dry) (4 mL) was added at 0° C. and the mixture was stirred at room temperature under nitrogen for 1 day. The mixture was quenched with water at 0° C. carefully. EtOAc and THF were added and the organic layer was separated, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane) and crystallized from THF/IPE to give the title compound (34.9 mg) as colorless crystals.

Workup

  1. stirringthe mixture was stirred at room temperature under nitrogen for 1 day
  2. customThe mixture was quenched with water at 0° C. carefully
  3. additionEtOAc and THF were added
  4. customthe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane)
  9. customcrystallized from THF/IPE

Sources & evidence

ORD record
ord-cd945ac485f44acda569d87a32b4ed65
Source dataset
uspto-grants-2014_12
Patent number
US08916551B2

Reaction notes

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