p-Anisoyl chloride → HCID 12069535, compound

HRID 1370644Notes

Reaction equation

HRID 1370644 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:10]([NH2:15])=[N:11][CH:12]=[CH:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Si](C)(C)[N-][Si](C)(C)C.[K+].[C:26](Cl)(=[O:35])[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C:9]1[C:10]([NH:15][C:26](=[O:35])[C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)=[N:11][CH:12]=[CH:13][CH:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 7477p-Anisoyl chlorideHCID 25517Ammonium ChlorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 13508831tert-Butyl hydrogen (2-aminopyridin-3-yl)carbonimidate

Product 1

HCID 12069535HCID 12069535, compoundYield 34.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N3-(tert-butoxycarbonyl)-2,3-pyridinediamine (446 mg, 2.13 mmol) in tetrahydrofuran (7 mL) was treated with potassium hexamethyldisilazide (894 mg, 4.48 mmol). After 0.1 hr, the mixture was treated with p-anisoyl chloride (0.365 mL, 2.13 mmol). After 0.5 hr, the mixture was poured into aqueous ammonium chloride solution and ethyl acetate. The organic layer was washed three times with water, once with saturated sodium chloride solution, dried (magnesium sulfate), and filtered. Concentration in vacuo and purification of the residue by flash chromatography (silica gel, hexanes/ethyl acetate) yielded 250 mg (34%) of the title compound.

Workup

  1. waitAfter 0.5 hr
  2. washThe organic layer was washed three times with water
  3. dry with materialonce with saturated sodium chloride solution, dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationConcentration
  6. customin vacuo and purification of the residue by flash chromatography (silica gel, hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-1858c206080742d6a3d83a7e3134b153
Source dataset
uspto-grants-2003_06
Patent number
US06583173B2

Reaction notes

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