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Potassium Carbonate → 1,1-Dimethylethyl 4-[(5'-{[({3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino) carbonyl]phenyl}methyl)(methyl)amino]methyl}-2'-fluoro-3-biphenylyl)methyl]-1-piperazinecarboxylate

HRID 564521
ノート
印刷プレビュー

反応式

HRID 564521 の反応式
Br[C:2]1[CH:3]=[C:4]([CH2:9][N:10]([CH2:12][C:13]2[CH:14]=[C:15]([CH:40]=[CH:41][CH:42]=2)[C:16]([NH:18][CH2:19][C:20]2[C:21]([NH:33][CH:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[C:22]3[CH:30]=[N:29][N:28]([CH2:31][CH3:32])[C:23]3=[N:24][C:25]=2[CH2:26][CH3:27])=[O:17])[CH3:11])[CH:5]=[CH:6][C:7]=1[F:8].[CH3:43][C:44]([O:47][C:48]([N:50]1[CH2:55][CH2:54][N:53]([CH2:56][C:57]2[CH:58]=[C:59](B(O)O)[CH:60]=[CH:61][CH:62]=2)[CH2:52][CH2:51]1)=[O:49])([CH3:46])[CH3:45].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:31]([N:28]1[C:23]2=[N:24][C:25]([CH2:26][CH3:27])=[C:20]([CH2:19][NH:18][C:16]([C:15]3[CH:14]=[C:13]([CH2:12][N:10]([CH2:9][C:4]4[CH:5]=[CH:6][C:7]([F:8])=[C:2]([C:59]5[CH:60]=[CH:61][CH:62]=[C:57]([CH2:56][N:53]6[CH2:54][CH2:55][N:50]([C:48]([O:47][C:44]([CH3:46])([CH3:45])[CH3:43])=[O:49])[CH2:51][CH2:52]6)[CH:58]=5)[CH:3]=4)[CH3:11])[CH:42]=[CH:41][CH:40]=3)=[O:17])[C:21]([NH:33][CH:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[C:22]2[CH:30]=[N:29]1)[CH3:32]
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 11430Potassium CarbonateHCID 42609723(3-((4-(Tert-butoxycarbonyl)piperazin-1-yl)methyl)phenyl)boronic acidHCID 578133763-{[[(3-Bromo-4-fluorophenyl)methyl](methyl)amino]methyl}-N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}benzamide

生成物 1

HCID 57813427
1,1-Dimethylethyl 4-[(5'-{[({3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino) carbonyl]phenyl}methyl)(methyl)amino]methyl}-2'-fluoro-3-biphenylyl)methyl]-1-piperazinecarboxylate
収率 82%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 218864351,4-Dioxane--water (1/1)溶媒

反応条件

温度
150 °C

実験手順

To a solution of 3-{[[(3-bromo-4-fluorophenyl)methyl](methyl)amino]methyl}-N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}benzamide (0.37 g, 0.58 mmol) in p-dioxane/H2O (4.5/1.5 mL) was added {3-[(4-{[(1,1-dimethylethyl)oxy]carbonyl}-1-piperazinyl)methyl]phenyl}boronic acid (0.279 g, 0.87 mmol), Pd(PPh3)4 (33.6 mg, 0.029 mmol), and K2CO3 (0.32 g, 2.32 mmol). The mixture was heated with a microwave at 150° C. for 15 min. The organic layer was separated and concentrated. The residue was redissolved in EtOAc, washed with H2O, brine, dried over Na2SO4, filtered, concentrated and the concentrate purified by CombiFlash chromatograph to afford the title compound 0.396 g (82%). LC-MS m/z 833 (M+H)+.

後処理

  1. customThe organic layer was separated
  2. concentrationconcentrated
  3. dissolutionThe residue was redissolved in EtOAc
  4. washwashed with H2O, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe concentrate purified by CombiFlash chromatograph

出典と根拠

ORDレコード
ord-420966e795424fc98d983be962a1851b
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08067408B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート