Potassium Carbonate → 1H-1,2,3-Triazolo[4,5-b]pyrazine, 1-[[(2S)-4-[5-[4-[(4-methyl-1-piperazinyl)methyl]phenyl]-2-pyrimidinyl]-2-morpholinyl]methyl]-6-(1-methyl-1H-pyrazol-4-yl)-

HRID 1478608ノート

反応式

HRID 1478608 の反応式
Br[C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12]C[C@H:10]([CH2:14][N:15]3[C:19]4=[N:20][C:21]([C:24]5[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=5)=[CH:22][N:23]=[C:18]4[N:17]=[N:16]3)[CH2:9]2)=[N:6][CH:7]=1.[CH3:30][N:31]1[CH2:36][CH2:35][N:34]([CH2:37][C:38]2[CH:43]=[CH:42][C:41](B3OC(C)(C)C(C)(C)O3)=[CH:40][CH:39]=2)[CH2:33][CH2:32]1.C([O-])([O-])=[O:54].[K+].[K+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:29][N:27]1[CH:28]=[C:24]([C:21]2[N:20]=[C:19]3[N:15]([CH2:14][C@H:10]4[O:54][CH2:12][CH2:13][N:8]([C:5]5[N:4]=[CH:3][C:2]([C:41]6[CH:40]=[CH:39][C:38]([CH2:37][N:34]7[CH2:33][CH2:32][N:31]([CH3:30])[CH2:36][CH2:35]7)=[CH:43][CH:42]=6)=[CH:7][N:6]=5)[CH2:9]4)[N:16]=[N:17][C:18]3=[N:23][CH:22]=2)[CH:25]=[N:26]1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 467390391-Methyl-4-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}piperazineHCID 118364803HCID 118364803、化合物

生成物 1

HCID 735047191H-1,2,3-Triazolo[4,5-b]pyrazine, 1-[[(2S)-4-[5-[4-[(4-methyl-1-piperazinyl)methyl]phenyl]-2-pyrimidinyl]-2-morpholinyl]methyl]-6-(1-methyl-1H-pyrazol-4-yl)-収率 71%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

(S)-1-((1-(5-bromopyrimidin-2-yl)piperidin-3-yl)methyl)-6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazine (250 mg, 0.55 mmol), 1-methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)benzyl)piperazine (210 mg, 0.66 mmol), Pd(dppf)2Cl2 (23 mg, 0.027 mmol), and K2CO3 (228 mg, 1.65 mmol) were dissolved in dioxane (6 ml)+H2O (1.5 ml), and then degassed with N2 (gas), followed by stirring at 80° C. for hours. After the completion of the reaction, the reaction mixture was extracted with H2O, EA, and brine, followed by drying (Na2SO4), filtration, and concentration under reduced pressure, and the residue was purified by column chromatography (MeOH:MC=1:10), to give (S)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)-4-(5-(4-((4-methylpiperazin-1-yl)methyl)phenyl)pyrimidin-2-yl)morpholine (210 mg, 71%).

後処理

  1. customdegassed with N2 (gas)
  2. customAfter the completion of the reaction
  3. extractionthe reaction mixture was extracted with H2O, EA, and brine
  4. customby drying
  5. filtration(Na2SO4), filtration, and concentration under reduced pressure
  6. customthe residue was purified by column chromatography (MeOH:MC=1:10)

出典と根拠

ORDレコード
ord-12873f22ccd64361b1fa3097a4c117c3
出典データセット
uspto-grants-2016_08
特許番号
US09403831B2

反応ノート

読み込み中…