Water → 5-[Benzyl-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-sulfonyl)-amino]-2-fluoro-N-isopropyl-benzamide

HRID 1186266ノート

反応式

HRID 1186266 の反応式
[CH2:1]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([F:21])=[C:13]([CH:20]=1)[C:14]([NH:16][CH:17]([CH3:19])[CH3:18])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[O:31]=[C:32]1[NH:37][C:36]2[CH:38]=[C:39]([S:42](Cl)(=[O:44])=[O:43])[CH:40]=[CH:41][C:35]=2[O:34][CH2:33]1.O>ClCCl>[CH2:1]([N:8]([S:42]([C:39]1[CH:40]=[CH:41][C:35]2[O:34][CH2:33][C:32](=[O:31])[NH:37][C:36]=2[CH:38]=1)(=[O:44])=[O:43])[C:9]1[CH:10]=[CH:11][C:12]([F:21])=[C:13]([CH:20]=1)[C:14]([NH:16][CH:17]([CH3:18])[CH3:19])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 52002293-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-sulfonyl chlorideHCID 673103385-Benzylamino-2-fluoro-N-isopropyl-benzamide

生成物 1

HCID 461825985-[Benzyl-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-sulfonyl)-amino]-2-fluoro-N-isopropyl-benzamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 5-benzylamino-2-fluoro-N-isopropyl-benzamide (30 mg, 0.1 mmol), diisopropylethylamine (37 μL, 0.2 mmol), and 3-oxo-3,4-dihydro-2H-1,4-benzooxazine-6-sulfonyl chloride (52 mg, 0.2 mmol) was refluxed in dry dichloromethane (3 ml) for 18 hrs. On cooling, water (10 ml) was added with stirring. The organic layer was separated, dried (PTFE frit), then concentrated in vacuo. The crude residue was purified by preparative TLC (10% v/v ethyl acetate/dichloromethane) to afford the title compound as an off white solid (23 mg). HPLC retention time 7.72 min. Mass spectrum (ES+) m/z 499 (M+H).

後処理

  1. temperatureOn cooling
  2. customThe organic layer was separated
  3. dry with materialdried (PTFE frit)
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by preparative TLC (10% v/v ethyl acetate/dichloromethane)

出典と根拠

ORDレコード
ord-e33b49c4f2d24327a2365c456cb4dd37
出典データセット
uspto-grants-2014_03
特許番号
US08673901B2

反応ノート

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