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

HRID 908315Notes

Reaction equation

HRID 908315 reaction equation
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[CH:44]=[CH:43][S:42][CH:41]=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[CH:44]=[CH:43][S:42][CH:41]=3)=[O:39])[CH:31]=[CH:30]4)[CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][N:6]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 67386422N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)thiophene-3-carboxamideHCID 673868285-bromo-N-(3-(dimethylamino)propyl)isoquinolin-1-amine

Product 1

HCID 58828836N-(6-(1-(3-(dimethylamino)propylamino)isoquinolin-5-yl)naphthalen-2-yl)thiophene-3-carboxamideYield 40%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a microwave vial containing 5-bromo-N-(3(dimethylamino)propyl) isoquinolin-1-amine (Step 5, 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-3-carboxamide (0.100 g, 0.3 mmol), Fibrecat catalyst (0.005 g, 5% by wt.), along with 2 M Potassium Carbonate (0.5 mL, 1 mmol). The reaction mixture was placed into CEM Microwave for 10 minutes at 80° C., while supplying 60 Watts of energy via power-max. The 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 an off-white amorphous solid after drying, which was titled product (0.023 g, 0.08 mmol). MS (ESI pos. ion) m/z: 481 (M+H). Calc'd Exact Mass for C29H28N4OS: 480

Workup

  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 an off-white amorphous solid
  6. customafter drying

Sources & evidence

ORD record
ord-a3825149c8b346c484fe402862c5fc2d
Source dataset
uspto-grants-2011_09
Patent number
US08017601B2

Reaction notes

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