Cesium carbonate → HCID 89761890, 화합물

HRID 528624노트

반응식

HRID 528624 반응식
[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

참가 물질

6

반응물 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

생성물 1

HCID 89761890HCID 89761890, 화합물수율 48.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-4073572583fc483bb34bef7d32ec8cc0
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346798B2

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