Methyl iodide → tert-butyl (5-(5-chloro-2-(4-(N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)sulfamoyl)-2,5-difluorophenoxy)-phenyl)benzo[d]isoxazol-3-yl)(methyl)carbamate

HRID 2203437노트

반응식

HRID 2203437 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][C:26]2[CH:31]=[C:30]([F:32])[C:29]([S:33](=[O:52])(=[O:51])[N:34]([CH2:40][C:41]3[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][C:42]=3[O:49][CH3:50])[C:35]3[S:39][N:38]=[CH:37][N:36]=3)=[CH:28][C:27]=2[F:53])=[C:6]([C:8]2[CH:9]=[CH:10][C:11]3[O:15][N:14]=[C:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:12]=3[CH:24]=2)[CH:7]=1.[H-].[Na+].I[CH3:57]>CN(C)C=O.C(OCC)(=O)C.[Cl-].[NH4+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][C:26]2[CH:31]=[C:30]([F:32])[C:29]([S:33](=[O:52])(=[O:51])[N:34]([CH2:40][C:41]3[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][C:42]=3[O:49][CH3:50])[C:35]3[S:39][N:38]=[CH:37][N:36]=3)=[CH:28][C:27]=2[F:53])=[C:6]([C:8]2[CH:9]=[CH:10][C:11]3[O:15][N:14]=[C:13]([N:16]([CH3:57])[C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[C:12]=3[CH:24]=2)[CH:7]=1

참가 물질

7

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 71558770tert-butyl (5-(5-chloro-2-(4-(N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)sulfamoyl)-2,5-difluorophenoxy)phenyl)benzo[d]isoxazol-3-yl)carbamate

생성물 1

HCID 131735789tert-butyl (5-(5-chloro-2-(4-(N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)sulfamoyl)-2,5-difluorophenoxy)-phenyl)benzo[d]isoxazol-3-yl)(methyl)carbamate

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 25517Ammonium Chloride용매

실험 절차

To a solution of tert-butyl (5-(5-chloro-2-(4-(N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)sulfamoyl)-2,5-difluorophenoxy)phenyl)benzo[d]isoxazol-3-yl)carbamate (1.09 g, 1.39 mmol) in N,N-dimethylformamide (3 mL) was added sodium hydride (0.061 g of a 60% dispersion in mineral oil, 1.53 mmol) and the reaction mixture was stirred for 10 minutes at ambient temperature. Iodomethane (87 μL, 1.39 mmol) was added and the reaction mixture for stirred for 30 minutes at ambient temperature. The reaction mixture was diluted with ethyl acetate (100 mL) and saturated aqueous ammonium chloride (10 mL). The organic phase was washed with water (2 5 mL) and brine (10 mL) dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography, eluting with a 0-50% gradient of ethyl acetate in hexanes to afford tert-butyl (5-(5-chloro-2-(4-(N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)sulfamoyl)-2,5-difluorophenoxy)-phenyl)benzo[d]isoxazol-3-yl)(methyl)carbamate as a colorless foam.

후처리

  1. stirringthe reaction mixture for stirred for 30 minutes at ambient temperature
  2. washThe organic phase was washed with water (2 5 mL) and brine (10 mL)
  3. dry with materialdried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography
  7. washeluting with a 0-50% gradient of ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-7573e6d66b43436b8d4b3c5c2c6b09e1
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365578B2

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