Triethylamine → 2-[(5-Chloro-1-methyl-2-oxo-1,2-dihydro-pyridin-3-ylamino)-(4-chloro-phenyl)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 2204312ノート

反応式

HRID 2204312 の反応式
O(S(C)(=O)=O)S(C)(=O)=O.[CH2:10]([O:12][C:13]([C:15]1[CH:19]=[CH:18][N:17]([CH:20]([CH3:22])[CH3:21])[C:16]=1[CH:23]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)O)=[O:14])[CH3:11].CCN(CC)CC.[NH2:39][C:40]1[C:41](=[O:48])[N:42]([CH3:47])[CH:43]=[C:44]([Cl:46])[CH:45]=1>C(Cl)Cl.O>[CH2:10]([O:12][C:13]([C:15]1[CH:19]=[CH:18][N:17]([CH:20]([CH3:22])[CH3:21])[C:16]=1[CH:23]([NH:39][C:40]1[C:41](=[O:48])[N:42]([CH3:47])[CH:43]=[C:44]([Cl:46])[CH:45]=1)[C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)=[O:14])[CH3:11]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 867031052-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl esterHCID 867031183-Amino-5-chloro-1-methylpyridin-2(1H)-one

生成物 1

HCID 867031172-[(5-Chloro-1-methyl-2-oxo-1,2-dihydro-pyridin-3-ylamino)-(4-chloro-phenyl)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
-30 °C

実験手順

Ms2O (18.65 mmol) was added at −30° C. to a solution of 2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester (Step E4) (9.32 mmol) and Et3N (46.6 mmol) in CH2Cl2 (60 mL) and stirred at −30° C. for 15 min. 3-Amino-5-chloro-1-methyl-1H-pyridin-2-one (Step L4) (11.19 mmol) was added and the mixture was stirred at −10° C. for 30 min. The mixture was diluted with H2O and extracted with CH2Cl2 (3×). The combined organic phases were washed successively with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography to afford the title compound as a white solid. ESI-MS: tR=1.37 min, [M+]+462/464 (LC-MS 1).

後処理

  1. stirringthe mixture was stirred at −10° C. for 30 min
  2. extractionextracted with CH2Cl2 (3×)
  3. washThe combined organic phases were washed successively with H2O and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-0f943e1bbd13487685a4a2f289a4f81f
出典データセット
uspto-grants-2016_06
特許番号
US09365576B2

反応ノート

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