Water → HCID 22291132, compound

HRID 967869Notes

Reaction equation

HRID 967869 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[C:7]([C:9]1[CH:34]=[CH:33][C:12]([C:13]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([CH3:32])=[C:20]([NH:22][C:23](=[O:31])[C:24]3[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=3)[CH:21]=2)=[O:14])=[CH:11][CH:10]=1)#[N:8].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[C:7]([C:9]1[CH:10]=[CH:11][C:12]([C:13]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([CH3:32])=[C:20]([NH:22][C:23](=[O:31])[C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:2][C:3]([O:5][CH3:6])=[O:4])=[CH:26][CH:25]=3)[CH:21]=2)=[O:14])=[CH:33][CH:34]=1)#[N:8]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 9799563HCID 9799563, compound

Product 1

HCID 22291132HCID 22291132, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Methyl bromoacetate (0.023 ml) was added to a suspension of N-[5-(4-cyanobenzamido)-2-methylphenyl]-4-hydroxybenzamide (0.06 g) and potassium carbonate (0.045 g) in DMF (3 ml) and the mixture was stirred and heated to 80° C. for 5 hours. The mixture was poured into water and extracted with ethyl acetate. The organic extract was dried (MgSO4) and evaporated. The residue was triturated under diethyl ether. The resultant solid was dried under vacuum at 55° C. to give the title compound as a solid (0.024 g); NMR Spectrum: (DMSOd6) 2.2 (s, 3H), 3.71 (s, 3H), 4.9 (s, 2H), 7.05 (d, 2H), 7.23 (d, 1H), 7.56 (d, 1H), 7.81 (s, 1H), 7.97 (m, 4H), 8.1 (d, 2H), 9.75 (s, 1H), 10.44 (s, 1H).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. dry with materialwas dried (MgSO4)
  4. customevaporated
  5. customThe residue was triturated under diethyl ether
  6. customThe resultant solid was dried under vacuum at 55° C.

Sources & evidence

ORD record
ord-0f1f08fd77be4d7f8c67869b056592a8
Source dataset
uspto-grants-2005_10
Patent number
US06956037B2

Reaction notes

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