Morpholine → 4-[(4-Chloro-5-methoxy-2-methylphenyl)amino]-7-methoxy-8-[2-(morpholin-4-yl)ethoxy]benzo[g]quinoline-3-carbonitrile

HRID 989360

반응식

HRID 989360 반응식
[Cl:1][C:2]1[C:30]([O:31][CH3:32])=[CH:29][C:5]([NH:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]4[CH:20]=[C:19]([O:21][CH2:22][CH2:23]Cl)[C:18]([O:25][CH3:26])=[CH:17][C:14]=4[CH:15]=3)[N:10]=[CH:9][C:8]=2[C:27]#[N:28])=[C:4]([CH3:33])[CH:3]=1.[Cl:34][C:35]1[C:63]([O:64][CH3:65])=[CH:62][C:38]([NH:39][C:40]2[C:49]3[C:44](=[CH:45][C:46]4[CH:53]=[C:52]([O:54][CH3:55])[C:51]([O:56][CH2:57][CH2:58]Cl)=[CH:50][C:47]=4[CH:48]=3)[N:43]=[CH:42][C:41]=2[C:60]#[N:61])=[C:37]([CH3:66])[CH:36]=1.C([O-])(=O)C.[Na+].[NH:72]1[CH2:77][CH2:76][O:75][CH2:74][CH2:73]1>>[Cl:1][C:2]1[C:30]([O:31][CH3:32])=[CH:29][C:5]([NH:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]4[CH:20]=[C:19]([O:21][CH2:22][CH2:23][N:72]5[CH2:77][CH2:76][O:75][CH2:74][CH2:73]5)[C:18]([O:25][CH3:26])=[CH:17][C:14]=4[CH:15]=3)[N:10]=[CH:9][C:8]=2[C:27]#[N:28])=[C:4]([CH3:33])[CH:3]=1.[Cl:34][C:35]1[C:63]([O:64][CH3:65])=[CH:62][C:38]([NH:39][C:40]2[C:49]3[C:44](=[CH:45][C:46]4[CH:53]=[C:52]([O:54][CH3:55])[C:51]([O:56][CH2:57][CH2:58][N:72]5[CH2:77][CH2:76][O:75][CH2:74][CH2:73]5)=[CH:50][C:47]=4[CH:48]=3)[N:43]=[CH:42][C:41]=2[C:60]#[N:61])=[C:37]([CH3:66])[CH:36]=1

참가 물질

6

반응물 4

HCID 8083MorpholineHCID 517045Sodium AcetateHCID 115113674-(4-Chloro-5-methoxy-2-methylanilino)-7-methoxy-8-(chloroethoxy)benzo[g]quinoline-3-carbonitrileHCID 116702254-(4-Chloro-5-methoxy-2-methylanilino)-8-methoxy-7-(chloroethoxy)benzo[g]quinoline-3-carbonitrile

생성물 2

HCID 53304264-(4-Chloro-5-methoxy-2-methylanilino)-8-methoxy-7-[2-(4-morpholinyl)ethoxy]benzo[g]quinoline-3-carbonitrileHCID 53304354-[(4-Chloro-5-methoxy-2-methylphenyl)amino]-7-methoxy-8-[2-(morpholin-4-yl)ethoxy]benzo[g]quinoline-3-carbonitrile수율 23%

반응 조건

온도
130 °C

실험 절차

A mixture of 318 mg (0.66 mmol) of 4-(4-chloro-5-methoxy-2-methylanilino)-7-methoxy-8-(chloroethoxy)benzo[g]quinoline-3-carbonitrile and 4-(4-chloro-5-methoxy-2-methylanilino)-8-methoxy-7-(chloroethoxy)benzo[g]quinoline-3-carbonitrile (1:1 mixture), 100 mg of sodium acetate and 5 mL of morpholine is stirred and heated to 130° C. using an oil bath. After 30 minutes the reaction is allowed to cool to room temperature. The reaction mixture is concentrated in vacuo and the residue purified by silica gel chromatography, eluting with 95:5 methylene chloride/methanol to yield 82 mg (23%) of 4-(4-chloro-5-methoxy-2-methylanilino)-7-methoxy-8-[2-(4-morpholinyl)ethoxy]benzo[g]quinoline-3-carbonitrile as a yellow wax and 153 mg of 4-(4-chloro-5-methoxy-2-methylanilino)-8-methoxy-7-[2-(4-morpholinyl)ethoxy]benzo[g]quinoline-3-carbonitrile as a yellow solid, mp 191-194° C. dec.

후처리

  1. temperatureto cool to room temperature
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. customthe residue purified by silica gel chromatography
  4. washeluting with 95:5 methylene chloride/methanol

출처 및 근거

ORD 기록
ord-65c7a782d6764cdc96372302cfaced9e
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06638929B2

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