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Trifluoroacetic acid → HCID 57813540, 화합물

HRID 564640
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HRID 564640 반응식
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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 224929571-Boc-4-(3-bromophenoxy)piperidineHCID 57813501HCID 57813501, 화합물

생성물 1

HCID 57813540HCID 57813540, 화합물수율 33.1%

시약·촉매·용매 4

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 962Water용매
HCID 6344Dichloromethane용매
HCID 312751,4-Dioxane용매

반응 조건

온도
130 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-433c4d99b9554dd5928bf4c2a11d7ede
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08067408B2

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