Water → N-(1-Ethyl-1H-pyrazol-3-yl)-3-[(9-fluoro-4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]-5-{[(S)-1-methyl-2-(methyloxy)ethyl]oxy}benzamide

HRID 548704ノート

反応式

HRID 548704 の反応式
CC([Si](C)(C)[O:6][CH2:7][CH2:8][N:9]([CH3:21])[C:10](=[O:20])[C:11]1[CH:16]=[CH:15][C:14](F)=[C:13]([F:18])[C:12]=1F)(C)C.[CH2:24]([N:26]1[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:46])[C:33]2[CH:38]=[C:37]([O:39][C@@H:40]([CH3:44])[CH2:41][O:42][CH3:43])[CH:36]=[C:35]([OH:45])[CH:34]=2)=[N:27]1)[CH3:25].C(=O)([O-])[O-].[K+].[K+].O>CC(N(C)C)=O>[CH2:24]([N:26]1[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:46])[C:33]2[CH:38]=[C:37]([O:39][C@@H:40]([CH3:44])[CH2:41][O:42][CH3:43])[CH:36]=[C:35]([O:45][C:14]3[CH:15]=[CH:16][C:11]4[C:10](=[O:20])[N:9]([CH3:21])[CH2:8][CH2:7][O:6][C:12]=4[C:13]=3[F:18])[CH:34]=2)=[N:27]1)[CH3:25]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 57663171N-(2-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}ethyl)-2,3,4-trifluoro-N-methylbenzamideHCID 59127176N-(1-Ethyl-1H-pyrazol-3-yl)-3-hydroxy-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}benzamide

生成物 1

HCID 15949499N-(1-Ethyl-1H-pyrazol-3-yl)-3-[(9-fluoro-4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]-5-{[(S)-1-methyl-2-(methyloxy)ethyl]oxy}benzamide収率 68.1%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
140 °C

実験手順

A suspension of N-(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)-2,3,4-trifluoro-N-methylbenzamide (300 mg, 0.86 mmol), N-(1-ethyl-1H-pyrazol-3-yl)-3-hydroxy-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}benzamide (290 mg, 0.91 mmol) and potassium carbonate (237 mg, 1.73 mmol) in DMA (20 mL) was heated to 140° C. for 4 hours. The reaction was poured into water (100 mL) and extracted with ethyl acetate (3×50 mL). The combined organic phases were washed with brine (50 mL) and dried (MgSO4), filtered and evaporated to give an orange oil. This was purified by column chromatography on alumina, eluting with 30-100% ethyl acetate in isohexane, to give the desired product as a colourless oil (300 mg).

後処理

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe combined organic phases were washed with brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto give an orange oil
  7. customThis was purified by column chromatography on alumina
  8. washeluting with 30-100% ethyl acetate in isohexane

出典と根拠

ORDレコード
ord-41f3497112704fce96f3dcc55df72470
出典データセット
uspto-grants-2011_05
特許番号
US07943607B2

反応ノート

読み込み中…