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Water → HCID 66728069, compound

HRID 573334
Notes
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Reaction equation

HRID 573334 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]=[C:3]1S(C)(=O)=O.[CH3:15][CH:16]([N:18]1[C:26]2[C:21](=[N:22][CH:23]=[CH:24][CH:25]=2)[C:20]([C:27]2[C:32](O)=[CH:31][CH:30]=[CH:29][N:28]=2)=[N:19]1)[CH3:17].[H-].[Na+].[OH2:36]>CN(C=O)C>[CH3:15][CH:16]([N:18]1[C:26]2[C:21](=[N:22][CH:23]=[CH:24][CH:25]=2)[C:20]([C:27]2[CH:32]=[CH:31][C:30]([O:36][C:3]3[N:2]([CH3:1])[C:6]4=[N:7][CH:8]=[CH:9][CH:10]=[C:5]4[N:4]=3)=[CH:29][N:28]=2)=[N:19]1)[CH3:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 585773713-Methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridineHCID 136409090HCID 136409090, compound

Product 1

HCID 66728069HCID 66728069, compound

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 3-methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine (174 mg) and 6-[(1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridin-3-yl]pyridin-3-ol (140 mg) in DMF (1.5 ml) was added NaH (60% in oil, 35.2 mg), and the mixture was stirred at 100° C. for 1 h. The mixture was heated at 180° C. for 30 min under microwave irradiation. The mixture was poured into water and extracted with AcOEt. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (AcOEt/hexane) and silica gel column chromatography (AcOEt/hexane). The eluent was evaporated and the residue was purified by preparative HPLC (C18, eluent: H2O/CH3CN (10 mM NH4HCO3)). The eluent was evaporated to give the title compound (68.1 mg).

Workup

  1. temperatureThe mixture was heated at 180° C. for 30 min under microwave irradiation
  2. extractionextracted with AcOEt
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (AcOEt/hexane) and silica gel column chromatography (AcOEt/hexane)
  8. customThe eluent was evaporated
  9. customthe residue was purified by preparative HPLC (C18, eluent: H2O/CH3CN (10 mM NH4HCO3))
  10. customThe eluent was evaporated

Sources & evidence

ORD record
ord-201c0c5494724204afa2f4c414acd520
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09029536B2

Reaction notes

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