Ethanesulfonylchloride, 2-chloro- → 9-(6-Methoxynaphthalen-2-yl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

HRID 1622721Notes

Reaction equation

HRID 1622721 reaction equation
[H-].[Na+].Cl[CH2:4][CH2:5][S:6](Cl)(=[O:8])=[O:7].[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[CH:18]=[C:17]([C:22]1[C:23]([NH2:28])=[N:24][CH:25]=[CH:26][CH:27]=1)[CH:16]=[CH:15]2>C1COCC1>[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[CH:18]=[C:17]([C:22]1[C:23]3=[N:28][S:6](=[O:8])(=[O:7])[CH2:5][CH2:4][N:24]3[CH:25]=[CH:26][CH:27]=1)[CH:16]=[CH:15]2

Participants

5

Reactant 3

HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 655501443-(6-Methoxynaphthalen-2-yl)pyridin-2-amine

Product 1

HCID 667483539-(6-Methoxynaphthalen-2-yl)-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%, 951 mg) in THF (dry) (40 ml) was added 2-chloroethanesulfonyl chloride (1.50 ml) at 0° C. and the mixture was stirred for 5 min at the same temperature. A solution of 3-(6-methoxynaphthalen-2-yl)pyridin-2-amine (1190 mg) in THF (dry) (25 mL) was added at 0° C. and the mixture was stirred at room temperature overnight. The mixture was quenched with water. Water and EtOAc were added and the precipitates were collected, washed with water/EtOAc, dried in vacuo to give the title compound (835.3 mg). A part of this was recrystallized from MeCN-THF/IPE.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe mixture was quenched with water
  3. additionWater and EtOAc were added
  4. customthe precipitates were collected
  5. washwashed with water/EtOAc
  6. customdried in vacuo

Sources & evidence

ORD record
ord-225776dd93a2453d8f0f94cda54742bd
Source dataset
uspto-grants-2014_07
Patent number
US08778934B2

Reaction notes

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