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Cesium carbonate → HCID 178420809、化合物

HRID 2200776
ノート
印刷プレビュー

反応式

HRID 2200776 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

HCID 178420809HCID 178420809、化合物収率 13.4%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 31275
1,4-Dioxane
溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-95324ee3ecdc4a93a95d88ce1b17a958
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09359380B2

反応ノート

読み込み中…

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