Methanol → N-(3,5-bis-trifluoromethyl-benzyl)-N-methyl-6-piperazin-1-yl-4-o-tolyl-nicotinamide

HRID 1017458

反応式

HRID 1017458 の反応式
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH3:26])[C:17]([C:27](=[O:45])[N:28]([CH2:30][C:31]3[CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[C:33]([C:41]([F:44])([F:43])[F:42])[CH:32]=3)[CH3:29])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.CO.[OH-].[Na+]>C(OCC)(=O)C>[F:43][C:41]([F:42])([F:44])[C:33]1[CH:32]=[C:31]([CH:36]=[C:35]([C:37]([F:39])([F:40])[F:38])[CH:34]=1)[CH2:30][N:28]([CH3:29])[C:27](=[O:45])[C:17]1[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])=[CH:19][C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[N:15][CH:16]=1

参加物

5

反応物 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 98523194-{5-[(3,5-Bis-trifluoromethyl-benzyl)-methyl-carbamoyl]-4-o-tolyl-pyridin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 10280286N-(3,5-bis-trifluoromethyl-benzyl)-N-methyl-6-piperazin-1-yl-4-o-tolyl-nicotinamide収率 87.4%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a solution of 6.60 g (104 mmol) 4-{5-[(3,5-bis-trifluoromethyl-benzyl)-methyl-carbamoyl]-4-o-tolyl-pyridin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester (Example 43) and 8.40 ml (207 mmol) methanol in 50 ml ethyl acetate 14.7 ml (207 mmol) acetyl chloride were added dropwise at 0° C. After 4 h the reaction mixture was diluted with ethyl acetate and treated with 1 N sodium hydroxide solution. The layers were separated and the aqueous layer extracted with dichloromethane. The combined organic layers were dried with sodium sulfate and concentrated to give 5.36 g of crude product. Flash column chromatography afforded 4.86 g (87.4%) of the title compound as a light brown solid.

後処理

  1. customThe layers were separated
  2. extractionthe aqueous layer extracted with dichloromethane
  3. dry with materialThe combined organic layers were dried with sodium sulfate
  4. concentrationconcentrated
  5. customto give 5.36 g of crude product

出典と根拠

ORDレコード
ord-e77bd9115f424472a531ad67dc32fc4a
出典データセット
uspto-grants-2002_11
特許番号
US06479483B2

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