Cesium carbonate → HCID 89761890、化合物

HRID 528624ノート

反応式

HRID 528624 の反応式
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][N:8]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)[S:9]([C:12]2[CH:13]=[CH:14][C:15]3[NH:20][CH2:19][CH2:18][O:17][C:16]=3[CH:21]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.F[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[S:36]([CH3:39])(=[O:38])=[O:37].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)[S:9]([C:12]2[CH:13]=[CH:14][C:15]3[N:20]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[S:36]([CH3:39])(=[O:38])=[O:37])[CH2:19][CH2:18][O:17][C:16]=3[CH:21]=2)(=[O:11])=[O:10])=[CH:27][CH:28]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 27782431-Fluoro-2-(methanesulfonyl)benzeneHCID 89761436N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

生成物 1

HCID 89761890HCID 89761890、化合物収率 48.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To a solution of INTERMEDIate M (300 mg, 0.717 mmol) and 1-fluoro-2-(methylsulfonyl)benzene (149.0 mg, 0.861 mmol, Apollo) in DMF was added cesium carbonate (467.0 mg, 1.43 mmol). The reaction mixture was heated at 90° C. for 16 h. After completion, the reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (2×10 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain the crude material which was purified by combiflash column chromatography (column size: 12 g; elution: 12% ethyl acetate in hexane) to provide N-(4-methoxybenzyl)-4-(2-(methylsulfonyl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (200 mg, 48.8%) as yellow solid. MS (ESI, positive ion) m/z: 572.02 (M+1).

後処理

  1. extractionextracted with ethyl acetate (2×10 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto obtain the crude material which
  5. customwas purified by combiflash column chromatography (column size: 12 g; elution: 12% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-4073572583fc483bb34bef7d32ec8cc0
出典データセット
uspto-grants-2016_05
特許番号
US09346798B2

反応ノート

読み込み中…