Cesium carbonate → HCID 22291099, compound

HRID 1369534Notes

Reaction equation

HRID 1369534 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:30])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[CH:19]=2)=[CH:12][C:11]=1[NH:31][C:32](=[O:40])[C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC(N(C)C)=O>O>[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:30])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[CH:19]=2)=[CH:12][C:11]=1[NH:31][C:32](=[O:40])[C:33]1[CH:34]=[CH:35][C:36]([O:39][C:2]2[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=2)=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 31374DimethylacetamideHCID 709434,6-DichloropyrimidineHCID 22291116HCID 22291116, compound

Product 1

HCID 22291099HCID 22291099, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4,6-Dichloropyrimidine (0.103 g) was added to a stirred mixture of N-[2-methyl-5-(3-morpholinobenzamido)phenyl]-4-hydroxybenzamide (0.3 g), caesium carbonate (0.453 g) and DMA (7.5 ml) and the resultant solution was stirred at ambient temperature for 18 hours. The mixture was poured into water (200 ml) and extracted with ethyl acetate. The organic phase was washed with water, dried (MgSO4) and evaporated. The residue was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and methanol as eluent. The material so obtained was triturated under diethyl ether. The resultant solid was isolated, washed with diethyl ether and dried under vacuum at 60° C. There was thus obtained the title compound (0.2 g); NMR Spectrum: (DMSOd6) 2.19 (s, 3H), 3.2 (t, 4H), 3.74 (t, 4H), 7.12 (m, 1H), 7.23 (m, 1H), 7.41 (m, 6H), 7.58 (m, 1H), 7.82 (d , 3H); 8.06 (d, 2H), 8.67 (s, 1H), 9.93 (s, 1H), 10.12 (s, 1H); Mass Spectrum: M+H+ 544.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica using
  6. temperatureincreasingly polar mixtures of methylene chloride and methanol as eluent
  7. customThe material so obtained
  8. customwas triturated under diethyl ether
  9. customThe resultant solid was isolated
  10. washwashed with diethyl ether
  11. customdried under vacuum at 60° C

Sources & evidence

ORD record
ord-d94970e1d5194c218e488afa4a48d32e
Source dataset
uspto-grants-2003_06
Patent number
US06579872B1

Reaction notes

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