4-Cyano-7-(4-methoxybenzylamino)-N,N,5-trimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide → 7-amino-4-cyano-N,N,5-trimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

HRID 17624Notes

Reaction equation

HRID 17624 reaction equation
[C:1]([C:3]1[C:8]2[N:9]=[C:10]([C:12]([N:14]([CH3:16])[CH3:15])=[O:13])[O:11][C:7]=2[C:6]([NH:17]CC2C=CC(OC)=CC=2)=[C:5]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:4]=1[CH3:33])#[N:2]>FC(F)(F)C(O)=O>[NH2:17][C:6]1[C:7]2[O:11][C:10]([C:12]([N:14]([CH3:16])[CH3:15])=[O:13])=[N:9][C:8]=2[C:3]([C:1]#[N:2])=[C:4]([CH3:33])[C:5]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

3

Reactant 1

HCID 685855194-Cyano-7-(4-methoxybenzylamino)-N,N,5-trimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

Product 1

HCID 685844087-amino-4-cyano-N,N,5-trimethyl-6-phenyl-1,3-benzoxazole-2-carboxamideYield 95.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

4-Cyano-7-(4-methoxybenzylamino)-N,N,5-trimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide (I-337) (2.10 g, 4.77 mmol) was dissolved in trifluoroacetic acid (22 ml), and stirred at room temperature for 13 hours. The solvent was evaporated away under reduced pressure, and the resulting residue was added to chloroform (25 ml) and an aqueous saturated sodium hydrogencarbonate solution (25 ml), followed by vigorously stirring for 15 minutes. The organic layer was separated, the aqueous layer was further extracted twice with chloroform. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, chloroform:acetone=98:2, v/v) to obtain the entitled compound (1.456 g, 95%) as a brown solid.

Workup

  1. customThe solvent was evaporated away under reduced pressure
  2. additionthe resulting residue was added to chloroform (25 ml)
  3. stirringby vigorously stirring for 15 minutes
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was further extracted twice with chloroform
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe insoluble matter was separated by filtration
  9. customthe solvent was evaporated away
  10. customthe resulting residue was purified by middle-pressure liquid chromatography (eluent, chloroform

Sources & evidence

ORD record
ord-8a98579b84314d95a827bc29a4492a5a
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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