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5-Tributylstannyl-1H-pyrazole-3-carboxylic acid ethyl ester → HCID 178468658, 화합물

HRID 906221
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인쇄 미리보기

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HRID 906221 반응식
C([Sn](CCCC)(CCCC)[C:6]1[NH:10][N:9]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=1)CCC.Br[C:25]1[N:30]2[N:31]=[CH:32][N:33]=[C:29]2[C:28]([NH:34][C:35]2[CH:40]=[CH:39][C:38]([N:41]3[CH2:46][C@@H:45]4[CH2:47][C@H:42]3[CH2:43][N:44]4[CH:48]([CH3:50])[CH3:49])=[CH:37][CH:36]=2)=[N:27][CH:26]=1>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:48]([N:44]1[CH2:43][C@@H:42]2[CH2:47][C@H:45]1[CH2:46][N:41]2[C:38]1[CH:37]=[CH:36][C:35]([NH:34][C:28]2[C:29]3[N:30]([N:31]=[CH:32][N:33]=3)[C:25]([C:6]3[NH:10][N:9]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=3)=[CH:26][N:27]=2)=[CH:40][CH:39]=1)([CH3:50])[CH3:49]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 149720685-Tributylstannyl-1H-pyrazole-3-carboxylic acid ethyl esterHCID 57963946(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-((1S,4S)-5-isopropyl-2,5-diazabicyclo[2.2.1]hept-2-yl)-phenyl]amine

생성물 1

HCID 178468658HCID 178468658, 화합물수율 28.7%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매
HCID 8028
Tetrahydrofuran
용매

실험 절차

A mixture of ethyl 5-(tributylstannyl)-1H-pyrazole-3-carboxylate (109.0 mg, 0.25 mmol) (Heterocyles, 1992, 813-818), (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-((1S,4S)-5-isopropyl-2,5-diazabicyclo[2.2.1]hept-2-yl)-phenyl]amine (163.0 mg, 0.38 mmol), and Pd(PPh3)2Cl2 (27.0 mg, 0.04 mmol) in THF (3 mL) is refluxed for 18 hours. After return to room temperature, solvent is removed under reduced pressure. Purification of the residue by silica gel column chromatography eluting with a mixture of DCM/7N NH3 in methanol (97/3) affords the title compound (35.0 mg, 28%).

후처리

  1. temperatureis refluxed for 18 hours
  2. customAfter return to room temperature, solvent is removed under reduced pressure
  3. customPurification of the residue by silica gel column chromatography
  4. washeluting with a mixture of DCM/7N NH3 in methanol (97/3)

출처 및 근거

ORD 기록
ord-7e2235aed0fa400fbc80c74f1675e617
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08012983B2

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