Hydrochloric Acid → HCID 68585307, compound

HRID 17390Notes

Reaction equation

HRID 17390 reaction equation
C[Al](C)C.[CH3:5][N:6]([CH3:12])[C:7](=[O:11])[CH2:8][NH:9][CH3:10].[C:13]([C:15]1[C:20]2[N:21]=[C:22]([C:24](OCC)=[O:25])[O:23][C:19]=2[C:18]([F:29])=[C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:16]=1[CH3:36])#[N:14].Cl>ClCCl>[C:13]([C:15]1[C:20]2[N:21]=[C:22]([C:24]([N:9]([CH2:8][C:7]([N:6]([CH3:12])[CH3:5])=[O:11])[CH3:10])=[O:25])[O:23][C:19]=2[C:18]([F:29])=[C:17]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:16]=1[CH3:36])#[N:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2063713N,N-dimethyl-2-(methylamino)acetamideHCID 16682925TrimethylaluminumHCID 51041426Ethyl 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate

Product 1

HCID 68585307HCID 68585307, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under nitrogen atmosphere, trimethylaluminium (1.03 M n-hexane solution, 1.19 ml, 1.23 mmol) was dropwise added at room temperature to a dichloromethane (2 ml) solution of N,N-dimethyl-2-methylaminoacetamide (143 mg, 1.23 mmol), and stirred for 35 minutes. Subsequently, a dichloromethane (2 ml) solution of ethyl 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate (I-111) (200 mg, 617 μmol) was dropwise added and stirred for 66.5 hours. After the reaction, aqueous 1 N hydrochloric acid solution was added to the reaction liquid with cooling with ice, followed by stirring at room temperature, and the reaction liquid was extracted with chloroform. Next, the obtained organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and the eluate with ethyl acetate gave the entitled compound (144 mg, 59%) as an amorphous substance.

Workup

  1. stirringstirred for 66.5 hours
  2. additionwas added to the reaction liquid
  3. temperaturewith cooling with ice
  4. stirringby stirring at room temperature
  5. customthe reaction liquid
  6. extractionwas extracted with chloroform
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8015a61a2f5145bba6f91635d98c16a7
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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