Sodium bis(trimethylsilyl)amide → 11-Descyclopropyl nevirapine

HRID 1734124ノート

反応式

HRID 1734124 の反応式
C1([NH:4][C:5]2[C:10]([C:11]([NH:13][C:14]3[C:15](OC)=[N:16][CH:17]=[CH:18][C:19]=3[CH3:20])=[O:12])=[CH:9][CH:8]=[CH:7][N:6]=2)CC1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>N1C=CC=CC=1>[CH3:20][C:19]1[C:14]2[NH:13][C:11](=[O:12])[C:10]3[CH:9]=[CH:8][CH:7]=[N:6][C:5]=3[NH:4][C:15]=2[N:16]=[CH:17][CH:18]=1

参加物

4

反応物 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 104474082-(Cyclopropylamino)-N-(2-methoxy-4-methyl-3-pyridinyl)-3-pyridinecarboxamide

生成物 1

HCID 2239900311-Descyclopropyl nevirapine収率 91%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
90 °C

実験手順

A solution of 2-(cyclopropylamino)-N-(2-methoxy-4-methyl-3-pyridinyl)-3-pyridinecarboxamide (0.3 g, 1 mmol) in 2 mL of dry pyridine under an argon atmosphere was treated with 2.2 mL of a 1.0M solution of NaHMDS. The solution was then warmed to 90° C. for 6 h. Upon cooling, the mixture was partitioned between EtOAc and 0.5N HCl. The EtOAc layer was then washed further with 0.5N HCl, dried (MgSO4) and concentrated. The residue was purified by flash chromatography on silica gel (1:1 EtOAc:Hexanes) to give 5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one in 91% yield (0.24 g).

後処理

  1. temperatureUpon cooling
  2. customthe mixture was partitioned between EtOAc and 0.5N HCl
  3. washThe EtOAc layer was then washed further with 0.5N HCl
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel (1:1 EtOAc:Hexanes)

出典と根拠

ORDレコード
ord-b78133a3db324dce86651e3cca1fe614
出典データセット
uspto-grants-1996_07
特許番号
US05532358

反応ノート

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