Triethylamine → HCID 22346273, compound

HRID 897293Notes

Reaction equation

HRID 897293 reaction equation
Br[C:2]1[N:11]=[C:10]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[C:17]=2[O:24][CH3:25])=[O:13])[C:9]([OH:26])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH3:27][N:28]([CH3:36])[C:29]1[CH:34]=[CH:33][C:32]([SH:35])=[CH:31][CH:30]=1.C(N(CC)CC)C>>[CH3:25][O:24][C:17]1[C:18]([O:22][CH3:23])=[CH:19][CH:20]=[CH:21][C:16]=1[CH2:15][NH:14][C:12]([C:10]1[C:9]([OH:26])=[C:8]2[C:3]([CH:4]=[CH:5][CH:6]=[N:7]2)=[C:2]([S:35][C:32]2[CH:33]=[CH:34][C:29]([N:28]([CH3:36])[CH3:27])=[CH:30][CH:31]=2)[N:11]=1)=[O:13]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 210614-(Dimethylamino)benzene-1-thiolHCID 223463785-bromo-N-(2,3-dimethoxybenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide

Product 1

HCID 22346273HCID 22346273, compound

Conditions

Temperature
135 °C

Procedure

Into a pressure reactor was placed 5-bromo-N-(2,3-dimethoxybenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide (0.1 g, 0.24 mmol), 4-(dimethylamino)benzenethiol (0.147 g, 0.96 mmol) and triethylamine (0.363 g, 0.5 mL, 3.59 mmol). The vessel was purged with nitrogen gas, sealed and heated to 135° C. for 18 hours, after which time it was cooled and the excess triethylamine removed in vacuo. The residue was partitioned between EtOAc/water and extracted. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and the solvent removed. The resulting glass was triturated with diethyl ether and filtered to yield N-(2,3-dimethoxybenzyl)-5-{[4-(dimethylamino)phenyl]thio}-8-hydroxy-1,6-naphthyridine-7-carboxamide as a solid.

Workup

  1. customInto a pressure reactor was placed
  2. customThe vessel was purged with nitrogen gas
  3. customsealed
  4. temperatureafter which time it was cooled
  5. customthe excess triethylamine removed in vacuo
  6. customThe residue was partitioned between EtOAc/water
  7. extractionextracted
  8. washThe combined organic extracts were washed with brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. customthe solvent removed
  12. customThe resulting glass was triturated with diethyl ether
  13. filtrationfiltered

Sources & evidence

ORD record
ord-fbb0488ce22f461d9ad2813292d40651
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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