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1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 54671227, 화합물

HRID 869046
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HRID 869046 반응식
Br[C:2]1[C:3]([NH2:20])=[N:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[N:7]=1.[C:21]([C:23]1[N:28]=[C:27]([NH2:29])[CH:26]=[CH:25][CH:24]=1)#[CH:22].C1CCN2C(=NCCC2)CC1>C(#N)C.[Pd]>[NH2:29][C:27]1[N:28]=[C:23]([C:21]#[C:22][C:2]2[C:3]([NH2:20])=[N:4][CH:5]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:10][CH:9]=3)[N:7]=2)[CH:24]=[CH:25][CH:26]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 450797916-Ethynylpyridin-2-amineHCID 580843723-Bromo-5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-amine

생성물 1

HCID 54671227HCID 54671227, 화합물수율 26%

시약·촉매·용매 2

HCID 23938Palladium촉매
HCID 6342
Acetonitrile
용매

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온도
100 °C

실험 절차

3-bromo-5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-amine (75 mg, 0.2105 mmol), 6-ethynylpyridin-2-amine (29.84 mg, 0.2526 mmol), Pd EnCat 30 (33.68 mg, 0.01347 mmol) and DBU (70.50 mg, 69.25 μL, 0.4631 mmol) were combined in acetonitrile (1.500 mL). The reaction mixture was heated at 100° C. under microwave conditions for 1.5 hours. After this time the solid residue was removed by filtration and the filtrate concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion™, 12 g column, eluting with 0 to 100% EtOAc/Petroleum Ether to 10% MeOH/DCM) to give the titled product as a beige solid (21 mg, 26% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.18 (d, 6H), 3.45 (sept, 1H), 6.20 (s, 2H), 6.52 (d, 1H), 7.06 (d, 1H), 7.07 (br s, 2H), 7.45 (dd, 1H), 7.90 (d, 2H), 8.25 (d, 2H) and 8.78 (s, 1H) ppm; MS (ES+) 394.1.

후처리

  1. customAfter this time the solid residue was removed by filtration
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was purified by column chromatography (ISCO Companion™, 12 g column, eluting with 0 to 100% EtOAc/Petroleum Ether to 10% MeOH/DCM)

출처 및 근거

ORD 기록
ord-6991d3d164384fbd9565a982b34f6c2b
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08969356B2

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