Dimethyl Sulfoxide → 2-(4-(8-((4-Methoxybenzyl)oxy)quinoline-4yl)piperazine-1yl)acetaldehyde

HRID 574291노트

반응식

HRID 574291 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][O:12][C:13]1[CH:39]=[CH:38][C:16]([CH2:17][O:18][C:19]2[CH:20]=[CH:21][CH:22]=[C:23]3[C:28]=2[N:27]=[CH:26][CH:25]=[C:24]3[N:29]2[CH2:34][CH2:33][N:32]([CH2:35][CH2:36][OH:37])[CH2:31][CH2:30]2)=[CH:15][CH:14]=1.CCN(CC)CC>C(Cl)Cl>[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][O:18][C:19]2[CH:20]=[CH:21][CH:22]=[C:23]3[C:28]=2[N:27]=[CH:26][CH:25]=[C:24]3[N:29]2[CH2:34][CH2:33][N:32]([CH2:35][CH:36]=[O:37])[CH2:31][CH2:30]2)=[CH:38][CH:39]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 675044332-(4-(8-((4-Methoxybenzyl)oxy)quinoline-4-yl)piperazine-1-yl)ethanol

생성물 1

HCID 866646662-(4-(8-((4-Methoxybenzyl)oxy)quinoline-4yl)piperazine-1yl)acetaldehyde수율 77%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of oxalyl chloride (1.8 mL, 20.33 mmol) in CH2Cl2 (40 mL) at −78° C. was added DMSO (2.8 mL, 40.66 mmol). The reaction mixture was stirred for 10 minutes followed by addition of compound 26 (4.0 g, 10.16 mmol, solution in 10 mL of CH2Cl2). The reaction mixture was stirred at the same temperature for 12 minutes. Then Et3N (8.4 mL, 60.98 mmol) was added and stirring was continued for another 1 hour and 20 minutes allowing the reaction mixture to come to room temperature. The reaction mixture was quenched by addition of water and extracted with CH2Cl2 (3×75 mL). The combined organic layer was washed with water and brine and finally purified by silica gel column chromatography (EtOAc/MeOH, 9.5:0.5) to yield 3.06 g (77%) of compound 27 as thick oil. 1H NMR (400 MHz, CDCl3) δ ppm 2.45-2.90 (m, 4H), 3.02-3.40 (m, 4H), 3.34 (s, 2H), 3.69 (s, 3H), 5.25 (s, 2H), 6.64-7.04 (m, 4H), 7.16-7.56 (m, 4H), 8.60-8.76 (m, 1H), 9.68 (s, 1H).

후처리

  1. stirringThe reaction mixture was stirred at the same temperature for 12 minutes
  2. stirringstirring
  3. waitwas continued for another 1 hour and 20 minutes
  4. customto come to room temperature
  5. customThe reaction mixture was quenched by addition of water
  6. extractionextracted with CH2Cl2 (3×75 mL)
  7. washThe combined organic layer was washed with water and brine
  8. customfinally purified by silica gel column chromatography (EtOAc/MeOH, 9.5:0.5)

출처 및 근거

ORD 기록
ord-3258d595d1984bf2830116c301c687c4
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034877B2

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