Potassium Carbonate → HCID 22291093, compound

HRID 967877Notes

Reaction equation

HRID 967877 reaction equation
[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][CH2:5][NH:6][CH3:7].F[C:10]1[CH:38]=[CH:37][C:13]([C:14]([NH:16][C:17]2[CH:18]=[CH:19][C:20]([CH3:36])=[C:21]([NH:23][C:24](=[O:35])[C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=3)[CH:22]=2)=[O:15])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][CH2:5][N:6]([C:10]1[CH:38]=[CH:37][C:13]([C:14]([NH:16][C:17]2[CH:18]=[CH:19][C:20]([CH3:36])=[C:21]([NH:23][C:24](=[O:35])[C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=3)[CH:22]=2)=[O:15])=[CH:12][CH:11]=1)[CH3:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 783021,3-Propanediamine, N1,N1,N3-trimethyl-HCID 22291037HCID 22291037, compound

Product 1

HCID 22291093HCID 22291093, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

N-(3-Dimethylaminopropyl)-N-methylamine (0.325 g) was added to a stirred mixture of N-[5-(4-fluorobenzamido)-2-methylphenyl]-3,4-dimethoxybenzamide (0.38 g), potassium carbonate (0.39 g) and DMSO (5 ml). The mixture was stirred and heated to 130° C. for 10 days. The mixture was allowed to cool to ambient temperature and partitioned between ethyl acetate and water. The organic phase was washed with water, dried (MgSO4) and evaporated to give an oil which was purified by column chromatography on silica gel using increasingly polar mixtures of methylene chloride and methanol as eluent. The material so obtained was triturated under diethyl ether and the resultant solid was dried under vacuum at 60° C. There was thus obtained the title compound (0.16 g), m.p. 164-165° C.; NMR Spectrum: (DMSOd6) 1.6 (m, 2H), 2.16 (s, 3H), 2.2 (s, 6H), 2.3 (t, 2H), 2.94 (s, 3H), 3.4 (t, 2H), 3.83 (s, 6H), 6.72 (d, 2H), 7.06 (d, 1H), 7.18 (d, 1H), 7.55 (m, 2H), 7.63 (m, 1H), 7.79 (d, 2H), 7.84 (d, 2H), 9.71 (br s, 1H), 9.8 (br s, 1H); Mass Spectrum: M+H+ 505; Elemental Analysis: Found C, 65.9; H, 7.0; N, 10.4; C29H36N4O4 1.3H2O requires C, 66.0; H, 7.4; N, 10.6%.

Workup

  1. temperatureto cool to ambient temperature
  2. custompartitioned between ethyl acetate and water
  3. washThe organic phase was washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give an oil which
  7. customwas purified by column chromatography on silica gel using
  8. temperatureincreasingly polar mixtures of methylene chloride and methanol as eluent
  9. customThe material so obtained
  10. customwas triturated under diethyl ether
  11. customthe resultant solid was dried under vacuum at 60° C

Sources & evidence

ORD record
ord-b1465824c405444d9d645feda81dd470
Source dataset
uspto-grants-2005_10
Patent number
US06956037B2

Reaction notes

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