Cyanogen Bromide → HCID 86711207, 화합물

HRID 1850789노트

반응식

HRID 1850789 반응식
[F:1][C:2]1[CH:19]=[C:18]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:17]=[CH:16][C:3]=1[O:4][CH2:5][CH2:6][C@@H:7]1[CH2:9][C@@H:8]1[CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+].[N:30]#[C:31]Br>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:19]=[C:18]([S:20]([CH3:23])(=[O:21])=[O:22])[CH:17]=[CH:16][C:3]=1[O:4][CH2:5][CH2:6][C@@H:7]1[CH2:9][C@@H:8]1[CH:10]1[CH2:11][CH2:12][N:13]([C:31]#[N:30])[CH2:14][CH2:15]1

참가 물질

5

반응물 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 867112054-((1R,2S)-2-{2-{2-fluoro-4-(methylsulfonyl)phenoxy]ethyl}cyclopropyl)piperidine

생성물 1

HCID 86711207HCID 86711207, 화합물

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

4-((1R,2S)-2-{2-{2-fluoro-4-(methylsulfonyl)phenoxy]ethyl}cyclopropyl)piperidine (Step C, Example 111; 150 mg, 0.428 mmol) and potassium carbonate (244 mg, 1.77 mmol) were stirred in chloroform (7 mL). Cyanogen bromide (61 mg, 0.58 mmol) was added. The mixture was stirred at RT for 15 min and refluxed overnight. The mixture was cooled to RT, mixed with silica gel (5 g), and concentrated to dryness under reduced pressure. The residue was loaded on a silica gel column (15 g of silica gel) and eluted with dichloromethane/methanol (97.5:2.5, 1 L to provide the title compound as an white solid. MS (Multimode) m/z 367 [M+H]+.

후처리

  1. temperaturerefluxed overnight
  2. temperatureThe mixture was cooled to RT
  3. additionmixed with silica gel (5 g)
  4. concentrationconcentrated to dryness under reduced pressure
  5. washeluted with dichloromethane/methanol (97.5:2.5, 1 L

출처 및 근거

ORD 기록
ord-7a63193e604d46cb8b95391c997fd4a7
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957062B2

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