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Toluene → Cyclohexyl-(6-methoxy-7-morpholin-4-yl-quinoxalin-2-yl)-amine

HRID 1060499
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HRID 1060499 반응식
C1(C)C=CC=CC=1.[CH:8]1([NH:14][C:15]2[CH:24]=[N:23][C:22]3[C:17](=[CH:18][C:19](Br)=[C:20]([O:25][CH3:26])[CH:21]=3)[N:16]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.CC(C)([O-])C.[Na+]>CCOCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH:8]1([NH:14][C:15]2[CH:24]=[N:23][C:22]3[C:17](=[CH:18][C:19]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[C:20]([O:25][CH3:26])[CH:21]=3)[N:16]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 1140TolueneHCID 8083MorpholineHCID 225731182-Cyclohexylamino-6-methoxy-7-bromo-quinoxalineHCID 23676156Sodium t-butoxide

생성물 1

HCID 22573158Cyclohexyl-(6-methoxy-7-morpholin-4-yl-quinoxalin-2-yl)-amine

시약·촉매·용매 2

HCID 6505921
(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium
촉매
HCID 3283Diethyl Ether용매

반응 조건

온도
80 °C

실험 절차

This preparation is based on an adaptation of the method described by Buchwald, et al, J. Am. Chem. Soc., 1996, 118, 7215. To a toluene solution of 2-cyclohexylamino-6-methoxy-7-bromo-quinoxaline (0.1 g, 0.3 mmol) under argon is added morpholine (0.1 g, 0.3 mmol), sodium tert-butoxide (0.04 g, 0.42 mmol), S-(−)-BINAP (cat., 0.001 g), and Pd(dba)2(cat., 0.001 g). The reaction mixture is heated to 80° C. overnight. The mixture is cooled, diluted with Et2O, filtered, concentrated, and chromatographed (50% EtOAc/hexanes). The product is recrystallized from EtOAc/hexanes to provide, in two crops, to provide a yellow solid (m.p. 194-196° C.). Anal. Calcd. for C19H26N4O2: C, 66.64; H, 7.65; N, 16.36; Found: C, 66.60; H, 7.60; N, 16.51.

후처리

  1. temperatureThe mixture is cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customchromatographed (50% EtOAc/hexanes)
  5. customThe product is recrystallized from EtOAc/hexanes
  6. customto provide, in two crops

출처 및 근거

ORD 기록
ord-42cc07312122456c9459d23350a9ba60
출처 데이터셋
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06524347B1

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