Triethylamine → 7-Fluoro-2-(2-furylmethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17557

反応式

HRID 17557 の反応式
ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C.[NH2:29][C:30]1[C:35]([OH:36])=[C:34]([F:37])[C:33]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[C:32]([CH3:44])[C:31]=1[C:45]#[N:46].[O:47]1[CH:51]=[CH:50][CH:49]=[C:48]1[CH2:52][C:53](O)=O>C(#N)C>[F:37][C:34]1[C:33]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[C:32]([CH3:44])[C:31]([C:45]#[N:46])=[C:30]2[C:35]=1[O:36][C:53]([CH2:52][C:48]1[O:47][CH:51]=[CH:50][CH:49]=1)=[N:29]2

参加物

7

反応物 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 75974Furan-2-acetic acidHCID 860974464-Amino-3-cyano-6-fluoro-5-hydroxy-2-methylbiphenyl

生成物 1

HCID 685849507-Fluoro-2-(2-furylmethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile収率 57%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

With cooling with ice, 1-hydroxybenzotriazole (134 mg, 0.991 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (174 mg, 0.908 mmol) and triethylamine (127 μl, 0.980 mmol) were added to an acetonitrile (8 ml) solution of 4-amino-6-fluoro-5-hydroxy-2-methylbiphenyl-3-carbonitrile (I-41) (200 mg, 0.826 mmol) and 2-furylacetic acid (115 mg, 0.908 mmol), followed by stirring at room temperature for 16 hours. The reaction liquid was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, and washed with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate, then concentrated under reduced pressure, and the resulting residue was dissolved in xylene (20 ml), then pyridinium p-toluenesulfonate (50 mg) was added, followed by heating under reflux in an oil bath at 160° C. for 1 hour. The reaction liquid was concentrated under reduced pressure, then the residue was dissolved in ethyl acetate, washed with saturated brine. After drying over anhydrous sodium sulfate, the insoluble matter was separated by filtration, and the residue obtained by concentration under reduced pressure was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=4:1, v/v) to obtain the entitled compound (155 mg, 57%) as a pale yellow solid.

後処理

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water and saturated brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. dissolutionthe resulting residue was dissolved in xylene (20 ml)
  8. additionpyridinium p-toluenesulfonate (50 mg) was added
  9. temperatureby heating
  10. temperatureunder reflux in an oil bath at 160° C. for 1 hour
  11. customThe reaction liquid
  12. concentrationwas concentrated under reduced pressure
  13. dissolutionthe residue was dissolved in ethyl acetate
  14. washwashed with saturated brine
  15. dry with materialAfter drying over anhydrous sodium sulfate
  16. customthe insoluble matter was separated by filtration
  17. customthe residue obtained by concentration under reduced pressure
  18. customwas purified by silica gel column chromatography (eluent, n-hexane

出典と根拠

ORDレコード
ord-4df9090a296049bea317dc08a09b52e6
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

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