Triethylamine → (S)-2-(5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-4-ylamino)-3,3-dimethylbutyl methanesulfonate

HRID 2171857ノート

反応式

HRID 2171857 の反応式
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]1[C:8]([NH:33][C@@H:34]([C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:35][OH:36])=[CH:9][C:10]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([F:22])[CH:20]=3)[N:15]([S:23]([C:26]3[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH:14]=2)=[N:11][CH:12]=1.C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:36][CH2:35][C@@H:34]([NH:33][C:8]1[C:7]([F:6])=[CH:12][N:11]=[C:10]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([F:22])[CH:20]=3)[N:15]([S:23]([C:26]3[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=3)(=[O:24])=[O:25])[CH:14]=2)[CH:9]=1)[C:37]([CH3:40])([CH3:39])[CH3:38])(=[O:4])=[O:3]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 71247626(S)-2-(5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-4-ylamino)-3,3-dimethylbutan-1-ol2 回

生成物 1

HCID 86714746(S)-2-(5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-4-ylamino)-3,3-dimethylbutyl methanesulfonate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Methanesulfonyl chloride (1.83 mL, 23.67 mmol) was added to a cold (0° C.) solution of (S)-2-(5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-4-ylamino)-3,3-dimethylbutan-1-ol, 54a, (9.50 g, 18.94 mmol) and triethylamine (3.30 mL, 23.67 mmol) in dichloromethane (118 mL). The reaction mixture was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure and the residue was diluted with water (100 mL) and EtOAc (200 mL). The organic layer was separated, dried (MgSO4), filtered and concentrated under reduced pressure to afford 10.5 g of the desired product as a pale yellow foam: LC/MS (60-90% ACN/water 5 min with 0.9% FA, C4) m/z 580.41 (M+H) RT=2.00 minutes.

後処理

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with water (100 mL) and EtOAc (200 mL)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-fef94572a639462699d0de21e37c9de4
出典データセット
uspto-grants-2015_06
特許番号
US09051319B2

反応ノート

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