Diisopropylethylamine → 6-{1-[(3S,4S)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethylamino}-nicotinonitrile

HRID 2191145노트

반응식

HRID 2191145 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][C@H:11]([CH:14]([NH2:16])[CH3:15])[C@@H:10]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:25]1[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][N:26]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][C@H:11]([CH:14]([NH:16][C:25]2[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][N:26]=2)[CH3:15])[C@@H:10]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 50057186-Bromopyridine-3-carbonitrileHCID 594381231-[(3S,4S)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethylamine

생성물 1

HCID 594381866-{1-[(3S,4S)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethylamino}-nicotinonitrile

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

A mixture of 610 mg (1.8 mmol) 1-[(3S,4S)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethylamine, 1.18 g (2.8 mmol) 2-bromo-5-cyano-pyridine and 0.838 g (2.8 mmol) DIPEA in 3.5 mL DMF was heated to 60° C. for 3 days. The mixture was evaporated, Na2CO3aq. was added and the mixture was extracted with ethyl acetate. The combined organic phases were dried with Na2SO4 and evaporated to dryness. The residue was purified by column chromatography on silica eluting with a gradient formed from DCM, methanol and NH3aq. to yield after evaporation of the product containing fractions 0.526 g (66%) of the title compound as off-white foam. MS (m/e): 431.4 [(M+H)+].

후처리

  1. customThe mixture was evaporated
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried with Na2SO4
  5. customevaporated to dryness
  6. customThe residue was purified by column chromatography on silica eluting with a gradient
  7. customformed from DCM, methanol and NH3aq
  8. customto yield
  9. customafter evaporation of the product
  10. additioncontaining fractions 0.526 g (66%) of the title compound as off-white foam

출처 및 근거

ORD 기록
ord-fd87ce8811a847ea83903bd58f58f6f6
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324248B2

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