Ethanesulfonylchloride, 2-chloro- → Tak-653

HRID 1748041ノート

反応式

HRID 1748041 の反応式
[H-].[Na+].Cl[CH2:4][CH2:5][S:6](Cl)(=[O:8])=[O:7].[CH:10]1([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[C:24]([NH2:30])=[N:25][CH:26]=[C:27]([CH3:29])[N:28]=3)=[CH:19][CH:18]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>C1COCC1>[CH:10]1([O:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3[C:24]4=[N:30][S:6](=[O:8])(=[O:7])[CH2:5][CH2:4][N:25]4[CH:26]=[C:27]([CH3:29])[N:28]=3)=[CH:21][CH:22]=2)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

参加物

5

反応物 3

HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 667484133-(4-(Cyclohexyloxy)phenyl)-5-methylpyrazin-2-amine

生成物 1

HCID 56655833Tak-653

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of NaH (60%, 5.29 g) in THF (dry) (100 mL) was added 2-chloroethanesulfonyl chloride (5.57 mL) at 0° C. and the mixture was stirred for 10 min at the same temperature. A solution of 3-(4-(cyclohexyloxy)phenyl)-5-methylpyrazin-2-amine (7.5 g) in THF (dry) (75 mL) was added at 0° C. and the mixture was stirred at room temperature under nitrogen for 2 days. The mixture was quenched with water/THF at 0° C. carefully and water was added to form precipitates which were washed with EtOAc and water and dried in vacuo to give crude title compound (4.7 g). The part of this material (ca. 4.3 g) was crystallized from DMSO (200 mL)-EtOH (40 ml)/water (400 mL) to give 9-[4-(cyclohexyloxy)phenyl]-7-methyl-3,4-dihydropyrazino[2,1-c][1,2,4]thiadiazine 2,2-dioxide as light-yellow crystals (3.6 g), which was recrystallized from DMSO (100 mL)-EtOH (15 mL)/water (100 mL) at 80° C. to room temperature to give the title compound (3.09 g) as light-yellow crystals.

後処理

  1. stirringthe mixture was stirred at room temperature under nitrogen for 2 days
  2. customThe mixture was quenched with water/THF at 0° C. carefully
  3. additionwater was added
  4. customto form
  5. customprecipitates which
  6. washwere washed with EtOAc and water
  7. customdried in vacuo
  8. customto give crude title compound (4.7 g)
  9. customThe part of this material (ca. 4.3 g) was crystallized from DMSO (200 mL)-EtOH (40 ml)/water (400 mL)

出典と根拠

ORDレコード
ord-32ccf2e81a464dd59efea97e31645056
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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