Cyanogen Bromide → HCID 86711207、化合物

HRID 1850789ノート

反応式

HRID 1850789 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 86711207HCID 86711207、化合物

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-7a63193e604d46cb8b95391c997fd4a7
出典データセット
uspto-grants-2015_02
特許番号
US08957062B2

反応ノート

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