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

HRID 17623Notes

Reaction equation

HRID 17623 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](F)=[C:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:4]=1[CH3:24])#[N:2].C(N(CC)CC)C.[CH3:32][O:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][NH2:39])=[CH:36][CH:35]=1>CS(C)=O>[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:39][CH2:38][C:37]2[CH:40]=[CH:41][C:34]([O:33][CH3:32])=[CH:35][CH:36]=2)=[C:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:4]=1[CH3:24])#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 754524-MethoxybenzylamineHCID 510423354-Cyano-7-fluoro-N,N,5-trimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

Product 1

HCID 685855194-Cyano-7-(4-methoxybenzylamino)-N,N,5-trimethyl-6-phenyl-1,3-benzoxazole-2-carboxamideYield 49%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

4-Cyano-7-fluoro-N,N,5-trimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide (I-114) (1.0 g, 3-09 mmol) was dissolved in dimethyl sulfoxide (60 ml), then at room temperature, triethylamine (560 μl, 4.02 mmol) was added, followed by heating at 150° C. 4-Methoxybenzylamine (525 μl, 4.02 mmol) was added to the solution all at a time, followed by stirring for 1.5 hours. The reaction liquid was cooled to room temperature, and the solvent was evaporated away under reduced pressure. The residue was fractionated with chloroform and saturated brine, and the organic layer was 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 (665 mg, 49%) as a yellow solid.

Workup

  1. customThe reaction liquid
  2. temperaturewas cooled to room temperature
  3. customthe solvent was evaporated away under reduced pressure
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. customThe insoluble matter was separated by filtration
  6. customthe solvent was evaporated away
  7. customthe resulting residue was purified by middle-pressure liquid chromatography (eluent, chloroform

Sources & evidence

ORD record
ord-762b01fb4f924551a3876c3729c0bd34
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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