Hydrochloric Acid → HCID 68585403, compound

HRID 17600Notes

Reaction equation

HRID 17600 reaction equation
Cl.[CH3:2][NH:3][CH3:4].C[Al](C)C.[Cl:9][C:10]1[CH:11]=[C:12]([C:16]2[C:29]([CH3:30])=[C:28]([C:31]#[N:32])[C:19]3[N:20]=[C:21]([C:23]([O:25]CC)=O)[O:22][C:18]=3[C:17]=2[F:33])[CH:13]=[CH:14][CH:15]=1.Cl>ClCCl>[Cl:9][C:10]1[CH:11]=[C:12]([C:16]2[C:29]([CH3:30])=[C:28]([C:31]#[N:32])[C:19]3[N:20]=[C:21]([C:23]([N:3]([CH3:4])[CH3:2])=[O:25])[O:22][C:18]=3[C:17]=2[F:33])[CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10473Dimethylamine, hydrochlorideHCID 16682925TrimethylaluminumHCID 68584448HCID 68584448, compound

Product 1

HCID 68585403HCID 68585403, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dimethylamine hydrochloride (1.406 g, 17.27 mmol) was suspended in dichloromethane (20 ml), and under nitrogen atmosphere at 0° C., trimethylaluminium (1.03 M n-hexane solution) (16.8 ml, 17.27 mmol) was gradually dropwise added. After stirring at room temperature for 30 minutes, a dichloromethane (20 ml) solution of ethyl 6-(3-chlorophenyl)-4-cyano-7-fluoro-5-methyl-1,3-benzoxazole-2-carboxylate (I-310) (2.065 g, 5.75 mmol) was dropwise added at 0° C. The solution was stirred for 21 hours with gradually heating up to room temperature, then at 0° C., aqueous 1 N hydrochloric acid solution (50 ml) was dropwise added, taking 15 minutes. After stirring at the same temperature for 30 minutes, the reaction liquid was extracted three times with dichloromethane. The organic layers were combined, washed with saturated brine, then 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=99:1, v/v) to obtain the entitled compound (1.641 g, 80%) as a pale yellow solid.

Workup

  1. stirringThe solution was stirred for 21 hours
  2. temperaturewith gradually heating up to room temperature
  3. waittaking 15 minutes
  4. stirringAfter stirring at the same temperature for 30 minutes
  5. customthe reaction liquid
  6. extractionwas extracted three times with dichloromethane
  7. washwashed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe insoluble matter was separated by filtration
  10. customthe solvent was evaporated away
  11. customthe resulting residue was purified by middle-pressure liquid chromatography (eluent, chloroform

Sources & evidence

ORD record
ord-bd6ae44a0d5347c0bfe14572abfdec15
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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