Sodium bis(trimethylsilyl)amide → 11-Descyclopropyl nevirapine

HRID 1734124노트

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HRID 1734124 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 2239900311-Descyclopropyl nevirapine수율 91%

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
90 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-b78133a3db324dce86651e3cca1fe614
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05532358

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