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Sodium Hydroxide → N4-(tert-butyloxycarbonyl)-N3-[4-(4-pyridyl)benzoyl]-3,4-pyridinediamine

HRID 1355625
Notes
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Reaction equation

HRID 1355625 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([O-:13])=O)=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.[Na+].C(Cl)(=O)C(Cl)=O.[C:23]([O:27][C:28]([NH:30][C:31]1[CH:36]=[CH:35][N:34]=[CH:33][C:32]=1[NH2:37])=[O:29])([CH3:26])([CH3:25])[CH3:24].[OH-].[Na+]>C(Cl)Cl.O1CCCC1.C(OCC)(=O)C.N1C=CC=CC=1.CN(C)C=O>[C:23]([O:27][C:28]([NH:30][C:31]1[CH:36]=[CH:35][N:34]=[CH:33][C:32]=1[NH:37][C:11](=[O:13])[C:10]1[CH:9]=[CH:8][C:7]([C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)=[CH:15][CH:14]=1)=[O:29])([CH3:26])([CH3:24])[CH3:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 4

HCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 110958633-Amino-4-(Boc-amino)pyridineHCID 23673507Sodium 4-(pyridin-4-yl)benzoate

Product 1

HCID 12069544N4-(tert-butyloxycarbonyl)-N3-[4-(4-pyridyl)benzoyl]-3,4-pyridinediamineYield 10%

Reagents, catalysts & solvents 5

HCID 1049
Pyridine
Solvent
HCID 6228DimethylformamideSolvent
HCID 6344DichloromethaneSolvent2×
HCID 8028TetrahydrofuranSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of sodium 4-(4-pyridyl)benzoate (425 mg, 1.92 mmol) in methylene chloride was treated with oxalyl chloride (0.840 mL, 9.60 mmol), followed by dimethylformamide (0.01 mL). After 0.75 h, the mixture was concentrated in vacuo. The residue was then dissolved in methylene chloride and added dropwise to a solution of N4-(tert-butyloxycarbonyl)-3,4-pyridinediamine (400 mg, 1.92 mmol) and pyridine (0.31 mL) in methylene chloride (2 mL) and tetrahydrofuran (1 mL). After 16 h, the mixture was poured into ethyl acetate and 1 N aqueous sodium hydroxide. The organic layer was washed once with 1 N aqueous sodium hydroxide, once with saturated sodium chloride solution, dried (potassium carbonate), and filtered. The residue was purified by flash chromatography (silica gel, ethyl acetate/hexanes) to yield 75 mg (10%) of the title compound.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionThe residue was then dissolved in methylene chloride
  3. waitAfter 16 h
  4. washThe organic layer was washed once with 1 N aqueous sodium hydroxide, once with saturated sodium chloride solution
  5. dry with materialdried (potassium carbonate)
  6. filtrationfiltered
  7. customThe residue was purified by flash chromatography (silica gel, ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-9cf874a533404ce7b80b8cc1979320cd
Source dataset
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06586459B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes