Potassium Carbonate → HCID 178522507, compound

HRID 1091539Notes

Reaction equation

HRID 1091539 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:7]([CH2:21][CH2:22][N:23]=3)[C:8]([NH:12][C:13](=[O:20])[C:14]3[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=3)=[N:9][C:10]=2[CH:11]=1.Br[CH2:25][CH2:26][N:27]1[CH:31]=[CH:30][CH:29]=[CH:28]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:27]1([CH2:26][CH2:25][O:1][C:2]2[CH:3]=[CH:4][C:5]3[C:6]4[N:7]([CH2:21][CH2:22][N:23]=4)[C:8]([NH:12][C:13](=[O:20])[C:14]4[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=4)=[N:9][C:10]=3[CH:11]=2)[CH:31]=[CH:30][CH:29]=[CH:28]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 116512251-(2-Bromoethyl)pyrroleHCID 178522503HCID 178522503, compound

Product 1

HCID 178522507HCID 178522507, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

The suspension of N-(8-Hydroxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)nicotinamide (example 2-1) 70.0 mg (0.23 mmol), N-(2-bromoethyl)pyrrole 47.6 mg (0.27 mmol) and potassium carbonate 126 mg (0.91 mmol) in N,N-dimethylformamide 5 mL was heated in a sealed tube to 120° C. for 3 hours. The reaction mixture was concentrated and partitioned between dichloromethane and water. The organic layer was washed with 0.1N NaOH solution and brine, dried over Na2SO4 and the solvent was evaporated to give the title compound 49.0 mg as off-white solid. Yield 54%.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between dichloromethane and water
  3. washThe organic layer was washed with 0.1N NaOH solution and brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-03f236830a3145c6902e4af3605fce07
Source dataset
uspto-grants-2012_03
Patent number
US08129386B2

Reaction notes

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