Ethanesulfonylchloride, 2-chloro- → 9-[4-(3-Ethylphenoxy)phenyl]-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

HRID 1747991ノート

反応式

HRID 1747991 の反応式
[H-].[Na+].Cl[CH2:4][CH2:5][S:6](Cl)(=[O:8])=[O:7].[CH2:10]([C:12]1[CH:13]=[C:14]([CH:29]=[CH:30][CH:31]=1)[O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:23]([NH2:28])=[N:24][CH:25]=[CH:26][CH:27]=2)=[CH:18][CH:17]=1)[CH3:11]>C1COCC1>[CH2:10]([C:12]1[CH:13]=[C:14]([CH:29]=[CH:30][CH:31]=1)[O:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[C:23]3=[N:28][S:6](=[O:8])(=[O:7])[CH2:5][CH2:4][N:24]3[CH:25]=[CH:26][CH:27]=2)=[CH:20][CH:21]=1)[CH3:11]

参加物

5

反応物 3

HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 667487013-(4-(3-Ethylphenoxy)phenyl)pyridin-2-amine

生成物 1

HCID 667481449-[4-(3-Ethylphenoxy)phenyl]-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of NaH (60%, 215 mg) in THF (dry) (20 mL) was added 2-chloroethanesulfonyl chloride (0.339 mL) at 0° C. and the mixture was stirred for 5 min at the same temperature. A solution of 3-(4-(3-ethylphenoxy)phenyl)pyridin-2-amine (312 mg) in THF (dry) (30 mL) was added at 0° C. and the mixture was stirred at room temperature for 1 hr. The mixture was quenched with water at 0° C. Water and EtOAc/THF were added and the extracted organic layer was washed with brine. Silica-gel was added to the organic layer and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc) and washed with IPE/EtOAc to give the title compound (295 mg) as a white solid. A part of this was recrystallized from THF/IPE.

後処理

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. customThe mixture was quenched with water at 0° C
  3. additionWater and EtOAc/THF were added
  4. washthe extracted organic layer was washed with brine
  5. additionSilica-gel was added to the organic layer
  6. customthe volatiles were removed in vacuo
  7. customwas purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc)
  8. washwashed with IPE/EtOAc

出典と根拠

ORDレコード
ord-76cd628d54194d9dbac97469d048d407
出典データセット
uspto-grants-2015_10
特許番号
US09150591B2

反応ノート

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