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Diisopropylethylamine → 4-[1-(5-Amino-2-fluoro-4-nitro-phenyl)-piperidin-4-ylideneaminooxy]-piperidine-1-carboxylic acid isopropyl ester

HRID 2066879
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HRID 2066879 반응식
[NH:1]1[CH2:6][CH2:5][C:4](=[N:7][O:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH2:3][CH2:2]1.Cl[C:22]1[C:23]([F:32])=[CH:24][C:25]([N+:29]([O-:31])=[O:30])=[C:26]([NH2:28])[CH:27]=1.C(N(C(C)C)CC)(C)C>CS(C)=O.C([O-])(O)=O.[Na+]>[CH:18]([O:17][C:15]([N:12]1[CH2:11][CH2:10][CH:9]([O:8][N:7]=[C:4]2[CH2:3][CH2:2][N:1]([C:22]3[CH:27]=[C:26]([NH2:28])[C:25]([N+:29]([O-:31])=[O:30])=[CH:24][C:23]=3[F:32])[CH2:6][CH2:5]2)[CH2:14][CH2:13]1)=[O:16])([CH3:20])[CH3:19]
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참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 5178355-Chloro-4-fluoro-2-nitroanilineHCID 57461147Isopropyl 4-(Piperidin-4-ylideneaminooxy)piperidine-1-carboxylate

생성물 1

HCID 866550194-[1-(5-Amino-2-fluoro-4-nitro-phenyl)-piperidin-4-ylideneaminooxy]-piperidine-1-carboxylic acid isopropyl ester

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide
용매
HCID 516892Sodium Bicarbonate용매

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온도
110 °C

실험 절차

2d (0.12 g), 5-chloro-4-fluoro-2-nitro-phenylamine (0.1 g) and diisopropylethylamine (0.1 mL) were combined in 1.2 mL of DMSO and stirred at 110° C. for 3 days. The mixture was cooled to room temperature, diluted with aqueous NaHCO3 (5 mL) and extracted with EtOAc (5 mL). The organic layer was concentrated under vacuum and purified on column chromatography (eluent: 10 to 50% EtOAc in hexane+0.1% triethylamine) to yield 60a.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with EtOAc (5 mL)
  3. concentrationThe organic layer was concentrated under vacuum
  4. custompurified on column chromatography (eluent: 10 to 50% EtOAc in hexane+0.1% triethylamine)

출처 및 근거

ORD 기록
ord-319a185b2a664847a3a24cbe558fceaf
출처 데이터셋
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08293729B2

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