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 2203437ノート

反応式

HRID 2203437 の反応式
[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

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒HCID 25517Ammonium Chloride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7573e6d66b43436b8d4b3c5c2c6b09e1
出典データセット
uspto-grants-2016_06
特許番号
US09365578B2

反応ノート

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