Cesium carbonate → Ethyl 6-(6-(3-ethylureido)pyridin-3-yl)-1-(2-methoxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 2243023노트

반응식

HRID 2243023 반응식
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10](B2OC(C)(C)C(C)(C)O2)=[CH:9][N:8]=1)=[O:5])[CH3:2].I[C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[N:29]([CH2:33][CH2:34][O:35][CH3:36])[CH:28]=[C:27]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[C:26]2=[O:42].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.[Pd].C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([NH:3][C:4](=[O:5])[NH:6][C:7]1[N:8]=[CH:9][C:10]([C:23]2[CH:24]=[C:25]3[C:30](=[CH:31][CH:32]=2)[N:29]([CH2:33][CH2:34][O:35][CH3:36])[CH:28]=[C:27]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[C:26]3=[O:42])=[CH:11][CH:12]=1)[CH3:2]

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 592084346-(3-Ethylureido)pyridine-3-boronic acid pinacol ester2회HCID 59208478Ethyl 6-iodo-1-[2-(methyloxy)ethyl]-4-oxo-1,4-dihydro-3-quinolinecarboxylate

생성물 1

HCID 59208515Ethyl 6-(6-(3-ethylureido)pyridin-3-yl)-1-(2-methoxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

시약·촉매·용매 3

HCID 57646695Palladium;tetraphenyl-lambda5-phosphane촉매HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
110 °C

실험 절차

A mixture of N-ethyl-N′-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)urea (Intermediate 1, 80 mg, 0.27 mmol), ethyl 6-iodo-1-(2-methoxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate (WO2006010733, 100 mg, 0.25 mmol), cesium carbonate (90 mg, 0.27 mmol), and Tetrakisphenylphosphine palladium (28.9 mg, 0.02 mmol) in dioxane (4 mL) and water (1 mL) was degassed with nitrogen for 30 minutes. The reaction mixture was then heated in a microwave for 1 h at 110° C. The reaction mixture was cooled to room temperature and filtered, then placed on high vacuum to remove residual solvent (59 mg). MS (ESP): 439 (M+H+) for C23H26N4O5; NMR: 9.34 (s, 1H), 8.61 (m, 2H), 8.45 (m, 1H), 8.10 (m, 1H), 8.09 (m, 2H), 7.54 (m, 1H), 4.62 (m, 2H), 4.25 (m, 2H), 3.71 (m, 2H), 3.57 (s, 3H), 3.21 (m, 2H), 1.30 (t, J=7 Hz, 3H), 1.11 (t, J=8 Hz, 3H).

후처리

  1. customwas degassed with nitrogen for 30 minutes
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered
  4. customto remove residual solvent (59 mg)

출처 및 근거

ORD 기록
ord-0b121e4ab7dd415d82270f905ac0474e
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07674801B2

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