9-{4-[3-(1,1-Difluoroethyl)phenoxy]phenyl}-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide → 9-{4-[3-(1,1-Difluoroethyl)phenoxy]phenyl}-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

HRID 2035905ノート

反応式

HRID 2035905 の反応式
[F:1][C:2]([C:5]1[CH:6]=[C:7]([CH:27]=[CH:28][CH:29]=1)[O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:20]3=[N:21][S:22](=[O:26])(=[O:25])[CH2:23][CH2:24][N:19]3[CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)([F:4])[CH3:3]>C1COCC1.CO.[Pt](=O)=O>[F:4][C:2]([C:5]1[CH:6]=[C:7]([CH:27]=[CH:28][CH:29]=1)[O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]2[C:20]3=[N:21][S:22](=[O:26])(=[O:25])[CH2:23][CH2:24][N:19]3[CH2:18][CH2:17][CH2:16]2)=[CH:13][CH:14]=1)([F:1])[CH3:3]

参加物

5

反応物 1

HCID 667487699-{4-[3-(1,1-Difluoroethyl)phenoxy]phenyl}-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

生成物 1

HCID 667486239-{4-[3-(1,1-Difluoroethyl)phenoxy]phenyl}-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide収率 34.2%

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-[3-(1,1-difluoroethyl)phenoxy]phenyl}-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (230 mg) in THF (dry) (20 mL) and MeOH (20 mL). The mixture was stirred at room temperature under hydrogen overnight. Activated carbon was added and the insoluble solid was removed by filtration through NH-silica gel/Celite pad (eluted with EtOAc) and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with MeOH in EtOAc) and concentrated. The residue was crystallized from EtOAc/hexane to give the title compound (79.4 mg) as colorless crystals.

後処理

  1. additionActivated carbon was added
  2. customthe insoluble solid was removed by filtration through NH-silica gel/Celite pad (eluted with EtOAc)
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by column chromatography (silica gel, eluted with MeOH in EtOAc)
  5. concentrationconcentrated
  6. customThe residue was crystallized from EtOAc/hexane

出典と根拠

ORDレコード
ord-4ff00fc45f2d4c27ac7f7035ff8ec86c
出典データセット
uspto-grants-2013_11
特許番号
US08575154B2

反応ノート

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