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Triethylamine → 6-[(3-{[Tert-butyl(dimethyl)silyl]oxy}propyl)amino]-2-chloro-5-fluoronicotinonitrile

HRID 2235937
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HRID 2235937 반응식
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Cl:9][C:10]1[N:17]=[C:16]([NH:18][CH2:19][CH2:20][CH2:21][OH:22])[C:15]([F:23])=[CH:14][C:11]=1[C:12]#[N:13].ClC1N=C(Cl)C(F)=CC=1C#N.CCN(CC)CC>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Si:1]([O:22][CH2:21][CH2:20][CH2:19][NH:18][C:16]1[C:15]([F:23])=[CH:14][C:11]([C:12]#[N:13])=[C:10]([Cl:9])[N:17]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
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참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 27338492,6-Dichloro-5-fluoro-3-pyridinecarbonitrileHCID 866045982-Chloro-5-fluoro-6-[(3-hydroxypropyl)amino]nicotinonitrile

생성물 1

HCID 866045976-[(3-{[Tert-butyl(dimethyl)silyl]oxy}propyl)amino]-2-chloro-5-fluoronicotinonitrile수율 98%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매
HCID 6344Dichloromethane용매2회

실험 절차

To a solution of t-butyidimethylsilyl chloride (0.73 9, 4.79 mmol) in CH2Cl2 (21 mL) was added 2-chloro-5fluoro-6-[(3-hydroxypropyl)amino]nicotinonitrile [prepared as in Example 302] and starting from 2,6dichloro-5fluoronicotinonitrile] (1.0 g, 4.35 mmol), followed by Et3N (0.48 9, 4.79 mmol) and DMAP (0.01 g, 0.09 mmol). The resulting cloudy mixture was stirred at rt for 18 h, and then diluted with CH2Cl2. The organic layer was washed with water, dried (MgSO4), filtered, and then concentrated under reduced pressure. The product (1.47 g, 98%) was isolated after silica gel flash chromatography (2:1 hexanes/EtOAc) as a white solid. 1H NMR (400 MHz, CD3OD) δ 7.46 (d, 1H), 3.67 (t, 2H), 3.49 (t, 2H), 1.77 (qt, 2H), 0.84 (s, 9H), 0.00 (s, 6H).

후처리

  1. washThe organic layer was washed with water
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-0a176ff3e7734a2a94eb8f5e34f65bf4
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07714004B2

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