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Trifluoroacetic acid → HCID 57813540、化合物

HRID 564640
ノート
印刷プレビュー

反応式

HRID 564640 の反応式
Br[C:2]1[CH:3]=[C:4]([O:8][CH:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1.[CH2:22]([N:24]1[C:28]2=[N:29][C:30]([CH2:69][CH3:70])=[C:31]([CH2:40][NH:41][C:42]([C:44]3[CH:49]=[CH:48][CH:47]=[C:46]([C:50]([NH:52][CH2:53][C:54]4[CH:59]=[CH:58][CH:57]=[C:56](B5OC(C)(C)C(C)(C)O5)[CH:55]=4)=[O:51])[CH:45]=3)=[O:43])[C:32]([NH:33][CH:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[C:27]2[CH:26]=[N:25]1)[CH3:23].C([O-])([O-])=O.[K+].[K+].C(O)(C(F)(F)F)=O>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.C(Cl)Cl>[CH2:22]([N:24]1[C:28]2=[N:29][C:30]([CH2:69][CH3:70])=[C:31]([CH2:40][NH:41][C:42]([C:44]3[CH:49]=[CH:48][CH:47]=[C:46]([C:50]([NH:52][CH2:53][C:54]4[CH:59]=[C:58]([C:2]5[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH:9]6[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]6)[CH:3]=5)[CH:57]=[CH:56][CH:55]=4)=[O:51])[CH:45]=3)=[O:43])[C:32]([NH:33][CH:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[C:27]2[CH:26]=[N:25]1)[CH3:23]
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

9

反応物 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 224929571-Boc-4-(3-bromophenoxy)piperidineHCID 57813501HCID 57813501、化合物

生成物 1

HCID 57813540HCID 57813540、化合物収率 33.1%

試薬・触媒・溶媒 4

HCID 178418397
HCID 178418397、化合物
触媒
HCID 962Water溶媒
HCID 6344Dichloromethane溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
130 °C

実験手順

To a solution of 1,1-dimethylethyl 4-[(3-bromophenyl)oxy]-1-piperidinecarboxylate (0.036 g, 0.100 mmol) in 1,4-dioxane (0.9 mL) and H2O (300 μL) was added N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N′-{[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}-1,3-benzenedicarboxamide (0.067 g, 0.1 mmol), Pd(Ph3P)4 (4.62 mg, 4.00 μmol), and K2CO3 (0.028 g, 0.200 mmol). This mixture was heated at 130° C. for 15 min. The reaction mixture was concentrated (Glas-Col) and purified with CombiFlash chromatograph. To the resultant material was added DCM (300 μL) and TFA (100 μL, 1.298 mmol) which was then stirred at room temperature for 30 min. The reaction mixture was concentrated (Glas-Col), purified using a Gilson HPLC (with 0.1% TFA), concentrated on a GeneVac EZ-2 and neutralized with an amine cartridge to afford 0.0237 g (33.1%) of the title compound. LC-MS m/z 716 (M+H)+; 1H NMR (400 MHz, CD3OD) δ ppm 1.39 (t, J=6.78 Hz, 3 H) 1.48 (t, J=6.90 Hz, 3 H) 1.80-1.97 (m, 2 H) 1.99-2.24 (m, 5 H) 3.09-3.28 (m, 4 H) 3.41 (t, J=9.29 Hz, 2 H) 3.66 (t, J=11.04 Hz, 2 H) 4.02 (d, J=8.78 Hz, 2 H) 4.33 (br. s., 1 H) 4.42-4.90 (m, 8 H) 6.61-6.85 (m, 1 H) 6.94-7.17 (m, 1 H) 7.21 (br. s, 2 H) 7.31-7.66 (m, 5 H) 8.04 (d, J=7.53 Hz, 2 H) 8.27 (br. s., 1 H) 8.35-8.44 (m, 1 H).

後処理

  1. concentrationThe reaction mixture was concentrated (Glas-Col)
  2. custompurified with CombiFlash chromatograph
  3. concentrationThe reaction mixture was concentrated (Glas-Col)
  4. custompurified
  5. concentrationconcentrated on a GeneVac EZ-2

出典と根拠

ORDレコード
ord-433c4d99b9554dd5928bf4c2a11d7ede
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…

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