Potassium Carbonate → HCID 16679489, compound

HRID 2232984Notes

Reaction equation

HRID 2232984 reaction equation
[N:1]1([C:8]2[C:13]([CH2:14][NH:15][C:16]3[N:20]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:22]=4[Cl:28])[CH:19]=[N:18][N:17]=3)=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:36][C:37]([NH2:39])=[O:38]>CN(C)C=O>[Cl:28][C:22]1[C:23]([Cl:27])=[CH:24][CH:25]=[CH:26][C:21]=1[N:20]1[CH:19]=[N:18][N:17]=[C:16]1[NH:15][CH2:14][C:13]1[C:8]([N:1]2[CH2:7][CH2:6][CH2:5][N:4]([CH2:36][C:37]([NH2:39])=[O:38])[CH2:3][CH2:2]2)=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 68705957HCID 68705957, compound

Product 1

HCID 16679489HCID 16679489, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 113A (250 mg, 0.597 mmol) in dimethylformamide (7 ml) was added potassium carbonate (165 mg, 1.194 mmol) and bromoacetamide (124 mg, 0.896 mmol). The reaction mixture was stirred at room temperature for 16 hours then poured onto ice water. The aqueous mixture was extracted with dichloromethane. The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash column chromatography using dichloromethane/methanol (80:20) to give the title compound (109 mg). MS (ESI+) m/z 475.6 (M+H)+; Rt=1.41. 1H NMR (DMSO-d6) δ 8,170 (s, 1H); 8,054 (d,1H); 7,832 (d,1H); 7,579(m,3H); 7,251 (s,1H); 7,112 (s,1H); 6,832 (dd,1H); 6,545 (t,1H); 4,338 (d, 2H); 3,423 (m,4H); 3,011 (s,2H); 2,772 (m,2H); 2,710 (m,2H); 1,856(m,2H).

Workup

  1. additionthen poured onto ice water
  2. extractionThe aqueous mixture was extracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-f6648a99243d4a98aee51bcea7987c3b
Source dataset
uspto-grants-2010_05
Patent number
US07709469B2

Reaction notes

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