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 2035905노트

반응식

HRID 2035905 반응식
[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]

참가 물질

5

반응물 1

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

생성물 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-dioxide수율 34.2%

시약·촉매·용매 3

HCID 345198Adams' catalyst촉매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4ff00fc45f2d4c27ac7f7035ff8ec86c
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575154B2

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