Tetrahydrofuran → 9-[(7-Methoxynaphthalen-2-yl)oxy]-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

HRID 1405704Notes

Reaction equation

HRID 1405704 reaction equation
[H-].[Na+].Cl[CH2:4][CH2:5][S:6](Cl)(=[O:8])=[O:7].C1COCC1.[CH3:15][O:16][C:17]1[CH:26]=[C:25]2[C:20]([CH:21]=[CH:22][C:23]([O:27][C:28]3[C:29]([NH2:34])=[N:30][CH:31]=[CH:32][CH:33]=3)=[CH:24]2)=[CH:19][CH:18]=1>O>[CH3:15][O:16][C:17]1[CH:26]=[C:25]2[C:20]([CH:21]=[CH:22][C:23]([O:27][C:28]3[C:29]4=[N:34][S:6](=[O:8])(=[O:7])[CH2:5][CH2:4][N:30]4[CH:31]=[CH:32][CH:33]=3)=[CH:24]2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 667485403-[(7-Methoxynaphthalen-2-yl)oxy]pyridin-2-amine

Product 1

HCID 667489799-[(7-Methoxynaphthalen-2-yl)oxy]-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxideYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of sodium hydride (60%, 375 mg), 2-chloroethanesulfonyl chloride (612 mg) and dehydrated THF (15 mL) was added a mixture of 3-[(7-methoxynaphthalen-2-yl)oxy]pyridin-2-amine (500 mg) and dehydrated THF (15 mL) at room temperature. The reaction mixture was stirred for 2 hr, water was added, and THF was evaporated under reduced pressure. The resulting precipitate was washed with water and diisopropyl ether to give the title compound (348 mg) as a pale-brown solid. The obtained solid was crystallized from acetonitrile and diisopropyl ether to give a pale-brown solid.

Workup

  1. additionwas added
  2. customTHF was evaporated under reduced pressure
  3. washThe resulting precipitate was washed with water and diisopropyl ether

Sources & evidence

ORD record
ord-5b416ac8cfc64e01a53921645af6ecfe
Source dataset
uspto-grants-2014_12
Patent number
US08916551B2

Reaction notes

Loading…