Ammonium Chloride → HCID 15908562, compound

HRID 1370646Notes

Reaction equation

HRID 1370646 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([C:7]([NH:9][C:10]2[C:15]([NH2:16])=[CH:14][CH:13]=[CH:12][N:11]=2)=[O:8])=[CH:5][CH:4]=1.C[Si](C)(C)[N-][Si](C)(C)C.[K+].[C:29]([C:33]1[CH:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][CH:34]=1)([CH3:32])([CH3:31])[CH3:30].[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[C:29]([C:33]1[CH:34]=[CH:35][C:36]([C:37]([NH:16][C:15]2[C:10]([NH:9][C:7](=[O:8])[C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:18][CH:17]=3)=[N:11][CH:12]=[CH:13][CH:14]=2)=[O:38])=[CH:40][CH:41]=1)([CH3:32])([CH3:30])[CH3:31]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 743724-tert-Butylbenzoyl chlorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 12069536HCID 12069536, compound

Product 1

HCID 15908562HCID 15908562, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N2-(4-methoxybenzoyl)-2,3-pyridinediamine (92 mg, 0.38 mmol) in tetrahydrofuran (1 mL) was treated with potassium hexamethyldisilazide (160 mg, 0.80 mmol). After 0.25 hr, the mixture was treated with 4-tert-butylbenzoyl chloride. After 0.75 hr, the mixture was poured into a mixture of aqueous ammonium chloride solution and ethyl acetate. The organic layer was washed twice with water, once with saturated sodium chloride solution, dried (magnesium sulfate), and filtered. Concentration in vacuo and purification of the residue by flash cromatography (silica gel, methylene chloride/ethyl acetate) followed by recrystallization from ethyl acetate/hexanes yielded 31 mg (20%) of the title compound.

Workup

  1. waitAfter 0.75 hr
  2. washThe organic layer was washed twice with water, once with saturated sodium chloride solution
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationConcentration
  6. customin vacuo and purification of the residue by flash cromatography (silica gel, methylene chloride/ethyl acetate)
  7. customfollowed by recrystallization from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-88a9fd959f1c45099e6c1647b2a3de67
Source dataset
uspto-grants-2003_06
Patent number
US06583173B2

Reaction notes

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