홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Potassium Carbonate → (+/-)-5-[(6'-methyl-2,3'-bipyridin-5-yl)methyl]-2-(tetrahydro-2H-pyran-3-yl)-2,5-dihydro-3H-pyrazolo[4,3-c]pyrido[3,2-e]pyridazin-3-one

HRID 2067114
노트
인쇄 미리보기

반응식

HRID 2067114 반응식
C[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:4][C:3]=1[CH2:14][N:15]1[C:20]2[N:21]=[CH:22][CH:23]=[CH:24][C:19]=2[C:18](=S)[C:17]([C:26](OCC)=[O:27])=[N:16]1.Cl.[O:32]1[CH2:37][CH2:36][CH2:35][CH:34]([NH:38][NH2:39])[CH2:33]1.[C:40](=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>C(O)C.O1CCOCC1.CN(C=O)C>[CH3:40][C:11]1[N:10]=[CH:9][C:8]([C:6]2[CH:5]=[CH:4][C:3]([CH2:14][N:15]3[C:20]4[N:21]=[CH:22][CH:23]=[CH:24][C:19]=4[C:18]4=[N:39][N:38]([CH:34]5[CH2:35][CH2:36][CH2:37][O:32][CH2:33]5)[C:26](=[O:27])[C:17]4=[N:16]3)=[CH:2][N:7]=2)=[CH:13][CH:12]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 66744316(Tetrahydro-2H-pyran-3-yl)hydrazine hydrochlorideHCID 86662100Ethyl 1-[(6-methyl-2,3'-bipyridin-5-yl)methyl]-4-thioxo-1,4-dihydropyrido[2,3-c]pyridazine-3-carboxylate

생성물 1

HCID 49763348(+/-)-5-[(6'-methyl-2,3'-bipyridin-5-yl)methyl]-2-(tetrahydro-2H-pyran-3-yl)-2,5-dihydro-3H-pyrazolo[4,3-c]pyrido[3,2-e]pyridazin-3-one

시약·촉매·용매 3

HCID 702Ethanol용매HCID 6228Dimethylformamide용매HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

Ethyl 1-[(6-methyl-2,3′-bipyridin-5-yl)methyl]-4-thioxo-1,4-dihydropyrido[2,3-c]pyridazine-3-carboxylate [(Example 6, Step 2), 125 mg, 0.299 mmol], (±)-tetrahydro-2H-pyran-3-ylhydrazine hydrochloride (91.0 mg, 0.599 mmol, 2 equiv) and potassium carbonate (414 mg, 2.99 mmol, 10 equiv) were combined in ethanol (10 mL), N,N′-dimethylformamide (3 mL) and dioxane (5 mL) at ambient temperature and after 5 minutes, were warmed to 80° C. for 4 hours. The mixture was cooled to ambient temperature, poured into sodium bicarbonate (100 mL, aqueous saturated) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 0:100; hexanes:ethyl acetate containing 10% methanol), providing the titled compound as a deep red solid: 1H-NMR (400 MHz, CDCl3) δ 9.02 (1H, d, J=2.1 Hz), 8.93 (1H, d, J=2.3 Hz), 8.75 (1H, dd, J=4.6, 1.8 Hz), 8.51 (1H, dd, J=8.1, 1.8 Hz), 8.16 (1H, dd, J=8.1, 2.4 Hz), 7.97 (1H, dd, J=8.2, 2.3 Hz), 7.66 (1H, dd, J=8.2, 0.6 Hz), 7.50 (1H, dd, J=7.9, 4.6 Hz), 7.24 (1H, d, J=8.1 Hz), 5.97 (1H, br s), 4.70-4.62 (1H, m), 4.01-3.94 (2H, m), 3.74 (1H, ap t, J=10.7 Hz), 3.49 (1H, br m), 3.45 (1H, dd, J=11.1, 3.4 Hz), 2.60 (3H, s), 2.21-2.05 (3H, m) ppm; high resolution mass spectrometry (ES+) m/z 454.1984 [(M+H)+; calculated for C25H24N7O2: 454.1986].

후처리

  1. temperatureThe mixture was cooled to ambient temperature
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. dry with materialThe combined organic extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel gradient chromatography (100:0 to 0:100; hexanes:ethyl acetate containing 10% methanol)

출처 및 근거

ORD 기록
ord-d3f27821ad52497582dfd0710332882d
출처 데이터셋
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08293744B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트