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Cesium carbonate → N-[(4-chlorophenyl)methyl]-6-(morpholinomethyl)-4-oxo-1-(phenylsulfanylmethyl)quinoline-3-carboxamide

HRID 1068011
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HRID 1068011 반응식
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([CH2:21][N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[CH:15][CH:14]=3)=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:36]1([S:42][CH2:43]Cl)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CN(C=O)C.ClCCl>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][N:22]4[CH2:23][CH2:24][O:25][CH2:26][CH2:27]4)[CH:17]=3)[N:12]([CH2:43][S:42][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH:11]=2)=[O:9])=[CH:4][CH:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 81623Chloromethyl phenyl sulphideHCID 178522870HCID 178522870, 화합물

생성물 1

HCID 9915062N-[(4-chlorophenyl)methyl]-6-(morpholinomethyl)-4-oxo-1-(phenylsulfanylmethyl)quinoline-3-carboxamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매
HCID 6344
Dichloromethane
용매

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온도
75 °C

실험 절차

A solution of N-(4-chlorobenzyl)-4-hydroxy-6-(4-morpholinylmethyl)-3-quinolinecarboxamide (0.21 gm) from Preparation No. 40 in DMF (4 mL) is treated with cesium carbonate (0.30 gm) and chloromethyl phenyl sulfide (0.08 mL). The mixture is tightly capped and heated to 75° C. for 8 hrs. The reaction mixture is allowed to cool to room temperature, diluted with dichloromethane (50 mL) and washed with water (2×10 mL), brine, dried (Na2SO4) and concentrated under reduced pressure. The crude product is purified by flash column chromatography eluting with 2% to 4% methanol in dichloromethane and then by recrystallization from ethyl acetate-hexanes to afford 0.19 gm of the title compound as a white solid.

후처리

  1. customThe mixture is tightly capped
  2. temperatureto cool to room temperature
  3. washwashed with water (2×10 mL), brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product is purified by flash column chromatography
  7. washeluting with 2% to 4% methanol in dichloromethane
  8. customby recrystallization from ethyl acetate-hexanes

출처 및 근거

ORD 기록
ord-8fe13cde981548eaaf7502beadeadcee
출처 데이터셋
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06248739B1

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