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Potassium Carbonate → N-(6-(1-(3-(dimethylamino)propylamino)isoquinolin-5-yl)naphthalen-2-yl)thiophene-2-carboxamide

HRID 908314
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HRID 908314 반응식
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[C:7]2[NH:12][CH2:13][CH2:14][CH2:15][N:16]([CH3:18])[CH3:17].CC1(C)C(C)(C)OB([C:27]2[CH:28]=[C:29]3[C:34](=[CH:35][CH:36]=2)[CH:33]=[C:32]([NH:37][C:38]([C:40]2[S:41][CH:42]=[CH:43][CH:44]=2)=[O:39])[CH:31]=[CH:30]3)O1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C(Cl)Cl.O>[CH3:17][N:16]([CH3:18])[CH2:15][CH2:14][CH2:13][NH:12][C:7]1[C:8]2[C:3](=[C:2]([C:27]3[CH:28]=[C:29]4[C:34](=[CH:35][CH:36]=3)[CH:33]=[C:32]([NH:37][C:38]([C:40]3[S:41][CH:42]=[CH:43][CH:44]=3)=[O:39])[CH:31]=[CH:30]4)[CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][N:6]=1
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참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 67386798N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)thiophene-2-carboxamideHCID 673868285-bromo-N-(3-(dimethylamino)propyl)isoquinolin-1-amine

생성물 1

HCID 58828870N-(6-(1-(3-(dimethylamino)propylamino)isoquinolin-5-yl)naphthalen-2-yl)thiophene-2-carboxamide수율 15%

시약·촉매·용매 3

HCID 962
Water
용매
HCID 6344Dichloromethane용매
HCID 312751,4-Dioxane용매

실험 절차

To a microwave vial containing 5-bromo-N-(3(dimethylamino)propyl) isoquinolin-1-amine (Step 4, 0.055 g, 0.2 mmol) in 1,4-Dioxane (2 mL), was added N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)thiophene-2-carboxamide (0.076 g, 0.2 mmol), Fibrecat catalyst (0.005 g, 5% by wt.), along with 2 M Potassium Carbonate (0.5 mL, 1 mmol). The mixture was placed into CEM Microwave for 10 minutes at 80° C., while supplying 60 Watts of energy via power-max. Then mixture was diluted with DCM and H2O, and extracted with DCM (3×10 mL). Then dried organics (over sodium sulfate) was filtered, and concentrated in-vacuo. The crude was purified on reverse-phase HPLC. This gave a light yellow amorphous solid after drying, which was titled product (0.026 g, 0.03 mmol). MS (ESI pos. ion) m/z: 481 (M+H). Calc'd Exact Mass for C29H28N4OS: 480

후처리

  1. extractionextracted with DCM (3×10 mL)
  2. filtrationThen dried organics (over sodium sulfate) was filtered
  3. concentrationconcentrated in-vacuo
  4. customThe crude was purified on reverse-phase HPLC
  5. customThis gave a light yellow amorphous solid
  6. customafter drying

출처 및 근거

ORD 기록
ord-ac03675c6a8b436082cfa2c7a7baf5f6
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08017601B2

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