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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
ノート
印刷プレビュー

反応式

HRID 2067114 の反応式
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
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

8

反応物 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

生成物 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

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 6228Dimethylformamide溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

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].

後処理

  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)

出典と根拠

ORDレコード
ord-d3f27821ad52497582dfd0710332882d
出典データセット
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08293744B2

反応ノート

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