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Sodium Iodide → 7-(2-[1,4']Bipiperidinyl-1'-yl-ethoxy)-6-methoxy-4-(4-phenoxy-phenylamino)-quinoline-3-carbonitrile

HRID 269782
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HRID 269782 반응식
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:20][CH:19]=3)=[C:10]([C:15]#[N:16])[CH:11]=[N:12]2)=[CH:7][C:6]=1[O:31][CH3:32].[N:33]1([CH:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.[I-].[Na+]>COCCOC>[N:33]1([CH:39]2[CH2:44][CH2:43][N:42]([CH2:2][CH2:3][O:4][C:5]3[CH:14]=[C:13]4[C:8]([C:9]([NH:17][C:18]5[CH:23]=[CH:22][C:21]([O:24][C:25]6[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=6)=[CH:20][CH:19]=5)=[C:10]([C:15]#[N:16])[CH:11]=[N:12]4)=[CH:7][C:6]=3[O:31][CH3:32])[CH2:41][CH2:40]2)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1
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참가 물질

5

반응물 3

HCID 5238Sodium IodideHCID 786071,4'-BipiperidineHCID 684631667-(2-Chloroethoxy)-6-methoxy-4-(4-phenoxyphenylamino)quinoline-3-carbonitrile

생성물 1

HCID 252550557-(2-[1,4']Bipiperidinyl-1'-yl-ethoxy)-6-methoxy-4-(4-phenoxy-phenylamino)-quinoline-3-carbonitrile수율 47.7%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane
용매

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온도
137.5 °C

실험 절차

A mixture of 222.5 mg (0.5 mmol) of 7-(2-chloroethoxy)-6-methoxy-4-(4-phenoxyphenylamino)quinoline-3-carbonitrile, 841.4 mg (5.0 mmol) of 4-piperidinopiperidine and 49.5 mg (0.33 mmol) of sodium iodide in 6.0 mL of ethylene glycol dimethyl ether are heated in a sealed tube at 135-140° C. for 17 hours to yield the crude product. Solvents are removed in vacuo. Purification of the oily residue is carried out by preparative thin layer chromatography (eluting with 85:15 dichloromethane/methanol) to provide 137.7 mg of 7-(2-[1,4′]bipiperidinyl-1′-yl-ethoxy)-6-methoxy-4-(4-phenoxy-phenylamino)-quinoline-3-carbonitrile as a light yellow solid, mp 141° C. (decompose).

후처리

  1. customto yield the crude product
  2. customSolvents are removed in vacuo
  3. customPurification of the oily residue
  4. washis carried out by preparative thin layer chromatography (eluting with 85:15 dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-9d44d3b9d57840fd968efdaa32841f6c
출처 데이터셋
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07449460B2

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