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Cesium carbonate → HCID 178420809, 화합물

HRID 525279
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HRID 525279 반응식
CS([O:5][CH:6]1[CH2:11][CH2:10][CH:9]([O:12][C:13]2[N:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:8][CH2:7]1)(=O)=O.[O:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:26]=[C:27](O)[C:28]3[N:29]=[CH:30][CH:31]=[N:32][C:33]=3[CH:34]=2)[CH2:21][CH2:20]1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.CCOC(C)=O>[N:14]1[CH:15]=[CH:16][CH:17]=[N:18][C:13]=1[O:12][C@H:9]1[CH2:10][CH2:11][C@H:6]([O:5][C:27]2[CH:26]=[C:25]([N:22]3[CH2:21][CH2:20][O:19][CH2:24][CH2:23]3)[CH:34]=[C:33]3[C:28]=2[N:29]=[CH:30][CH:31]=[N:32]3)[CH2:7][CH2:8]1
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참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 90413334(4-Pyrimidin-2-yloxycyclohexyl) methanesulfonateHCID 1366295107-Morpholinoquinoxalin-5-ol

생성물 1

HCID 178420809HCID 178420809, 화합물수율 13.4%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 31275
1,4-Dioxane
용매

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온도
110 °C

실험 절차

As shown in step 7-iv of Scheme 7, a mixture of (4-pyrimidin-2-yloxycyclohexyl) methanesulfonate (105 mg, 0.386 mmol), 7-morpholinoquinoxalin-5-ol (178.3 mg, 0.7712 mmol), and Cs2CO3 (125.6 mg, 0.3856 mmol) in dioxane (1.5 mL) was sealed in a 5 mL microwave tube and heated to 110° C. for 14 hours using an oil bath. The reaction mixture was cooled to room temperature, diluted with EtOAc, and filtered through diatomaceous earth which was subsequently washed with ethyl acetate. The filtrate was concentrated under reduced pressure and the residue purified via preparative reversed-phase HPLC (10-90% CH3CN/water gradient containing 0.1% TFA). Fractions containing a mixture of cis and trans isomers were further purified via SFC using a chiral OJ column and eluting with 40% MeOH in CO2 to provide 21 mg of 4-(8-(((trans)-4-(pyrimidin-2-yloxy)cyclohexyl)oxy)quinoxalin-6-yl)morpholine (compound 34): 1H NMR (300 MHz, Chloroform-d) δ 8.69 (dd, J=3.4, 1.9 Hz, 1H), 8.62 (dd, J=3.6, 1.9 Hz, 1H), 8.51 (dd, J=4.8, 2.2 Hz, 2H), 7.01-6.83 (m, 3H), 5.18 (tt, J=7.0, 3.4 Hz, 1H), 4.79 (tt, J=6.9, 3.1 Hz, 1H), 4.00-3.85 (m, 4H), 3.34 (dq, J=4.8, 2.6 Hz, 4H), 2.44-2.16 (m, 4H), 1.92 (tdd, J=16.4, 7.7, 2.8 Hz, 4H); ESMS (M+H+)=408.56, and 22 mg of 4-(8-(((cis)-4-(pyrimidin-2-yloxy)cyclohexyl)oxy)-quinoxalin-6-yl)morpholine (compound 42): 1H NMR (300 MHz, Chloroform-d) δ 8.70 (d, J=1.9 Hz, 1H), 8.63 (d, J=1.9 Hz, 1H), 8.52 (d, J=4.8 Hz, 2H), 7.01-6.87 (m, 3H), 5.17 (ddt, J=8.7, 6.7, 3.4 Hz, 1H), 4.76-4.58 (m, 1H), 4.00-3.87 (m, 4H), 3.40-3.27 (m, 4H), 2.43-2.22 (m, 4H), 2.05-1.87 (m, 2H), 1.86-1.71 (m, 2H); ESMS (M+H+)=408.56.

후처리

  1. customwas sealed in a 5 mL microwave tube
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered through diatomaceous earth which
  4. washwas subsequently washed with ethyl acetate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue purified via preparative reversed-phase HPLC (10-90% CH3CN/water gradient containing 0.1% TFA)
  7. additionFractions containing
  8. additiona mixture of cis and trans isomers
  9. customwere further purified via SFC
  10. washeluting with 40% MeOH in CO2

출처 및 근거

ORD 기록
ord-e6837d38e79e45eebebf3bbcda4f576b
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09340557B2

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