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Phenol → HCID 10160432, compound

HRID 897280
Notes
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Reaction equation

HRID 897280 reaction equation
Br[C:2]1[N:11]=[C:10]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=2)=[O:13])[C:9]([OH:24])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[C:25]1([OH:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C([O-])([O-])=O.[Na+].[Na+]>CN1C(=O)N(C)CCC1>[Cl:23][C:18]1[CH:17]=[C:16]([CH:21]=[C:20]([Cl:22])[CH:19]=1)[CH2:15][NH:14][C:12]([C:10]1[C:9]([OH:24])=[C:8]2[C:3]([CH:4]=[CH:5][CH:6]=[N:7]2)=[C:2]([O:31][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:11]=1)=[O:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 996PhenolHCID 10340Sodium CarbonateHCID 10796Cesium carbonateHCID 10180885HCID 10180885, compound

Product 1

HCID 10160432HCID 10160432, compound

Reagents, catalysts & solvents 1

HCID 81646
2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-
Solvent

Procedure

To a solution of 5-bromo-N-(3,5-dichlorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide from Example 50 (26 mg, 0.068 mmol), phenol (28 mg, 0.304 mmol) and cesium carbonate (198 mg, 0.608 mmol) in DMPU (0.25 ml) was heated at 140C for 8 hrs. The reaction was poured into sat aq. Na2CO3 and extracted with CHCl3. The organic phase was washed with water and dried (Na2SO4). The solvent was evaporated in vacuo and the residue dissolved in DMF (0.7 ml) and purified by preparative HPLC. (Gilson semi preparative HPLC system and a YMC Combiprep Pro Column (50×20 mm I.D., C18, S-5 um, 120A) eluting with 5-95% acetonitrile/water (0.1% TFA) at 15 ml/min) to afford the title compound after lyophilization.

Workup

  1. additionThe reaction was poured
  2. extractionextracted with CHCl3
  3. washThe organic phase was washed with water
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated in vacuo
  6. dissolutionthe residue dissolved in DMF (0.7 ml)
  7. custompurified by preparative HPLC
  8. wash(Gilson semi preparative HPLC system and a YMC Combiprep Pro Column (50×20 mm I.D., C18, S-5 um, 120A) eluting with 5-95% acetonitrile/water (0.1% TFA) at 15 ml/min)

Sources & evidence

ORD record
ord-386a1c819b194ed9b959d97037d619a5
Source dataset
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06921759B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes