HCID 66747700、化合物 → 9-[4-(4-Fluoro-3-methoxyphenoxy)phenyl]-7-methyl-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

HRID 1748029ノート

反応式

HRID 1748029 の反応式
[F:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[C:18]4=[N:19][S:20](=[O:24])(=[O:23])[CH2:21][CH2:22][N:17]4[CH:16]=[C:15]([CH3:25])[CH:14]=3)=[CH:9][CH:8]=2)=[CH:4][C:3]=1[O:28][CH3:29]>C1COCC1.CO.[Pt](=O)=O>[F:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([CH:13]3[C:18]4=[N:19][S:20](=[O:24])(=[O:23])[CH2:21][CH2:22][N:17]4[CH2:16][CH:15]([CH3:25])[CH2:14]3)=[CH:11][CH:12]=2)=[CH:4][C:3]=1[O:28][CH3:29]

参加物

5

反応物 1

HCID 66747700HCID 66747700、化合物

生成物 1

HCID 667480489-[4-(4-Fluoro-3-methoxyphenoxy)phenyl]-7-methyl-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide収率 7.5%

試薬・触媒・溶媒 3

HCID 345198Adams' catalyst触媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Platinum(IV) oxide (30 mg) was added to a solution of 9-[4-(4-fluoro-3-methoxyphenoxy)phenyl]-7-methyl-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (400 mg) in THF (dry) (15 mL) and MeOH (15 mL). The mixture was stirred at room temperature under hydrogen for 3 hr. Activated carbon was added and the insoluble solid was removed by filtration through silica gel/Celite pad (eluted with EtOAc). Platinum(IV) oxide (30 mg) was added and the mixture was stirred at room temperature under hydrogen overnight. AcOH (10 mL) and platinum(IV) oxide (30 mg) were added and the mixture was stirred at room temperature under hydrogen for 1 day and at 50° C. for 1 day. Activated carbon was added and the insoluble solid was removed by filtration through silica gel/Celite pad (eluted with EtOAc) and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc) and concentrated in vacuo. The residue was crystallized from THF/IPE to give the title compound (30.3 mg) as colorless crystals.

後処理

  1. additionActivated carbon was added
  2. customthe insoluble solid was removed by filtration through silica gel/Celite pad (eluted with EtOAc)
  3. additionPlatinum(IV) oxide (30 mg) was added
  4. stirringthe mixture was stirred at room temperature under hydrogen overnight
  5. additionAcOH (10 mL) and platinum(IV) oxide (30 mg) were added
  6. stirringthe mixture was stirred at room temperature under hydrogen for 1 day and at 50° C. for 1 day
  7. additionActivated carbon was added
  8. customthe insoluble solid was removed by filtration through silica gel/Celite pad (eluted with EtOAc)
  9. concentrationthe filtrate was concentrated in vacuo
  10. customThe residue was purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc)
  11. concentrationconcentrated in vacuo
  12. customThe residue was crystallized from THF/IPE

出典と根拠

ORDレコード
ord-31999f6f91c24b7f9171ce7e1bd45e3d
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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