Triethylamine → Benzyl [(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)methyl]methylcarbamate

HRID 17559ノート

反応式

HRID 17559 の反応式
ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C.[NH2:30][C:31]1[C:36]([OH:37])=[C:35]([F:38])[C:34]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[C:33]([CH3:45])[C:32]=1[C:46]#[N:47].[CH2:48]([O:55][C:56]([N:58]([CH3:63])[CH2:59][C:60](O)=O)=[O:57])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C(C)=CC=CC=1.C(#N)C>[C:46]([C:32]1[C:31]2[N:30]=[C:60]([CH2:59][N:58]([CH3:63])[C:56](=[O:57])[O:55][CH2:48][C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[O:37][C:36]=2[C:35]([F:38])=[C:34]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33]=1[CH3:45])#[N:47]

参加物

9

反応物 6

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 97053N-CarbobenzoxysarcosineHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 860974464-Amino-3-cyano-6-fluoro-5-hydroxy-2-methylbiphenyl

生成物 1

HCID 86630878Benzyl [(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)methyl]methylcarbamate収率 46%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 7237O-Xylene溶媒

実験手順

At room temperature, 1-hydroxybenzotriazole (184 mg, 1.36 mmol), 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride (249 mg, 1.30 mmol) and triethylamine (190 μl, 1.36 mmol) were added to an acetonitrile (12 ml) solution of 4-amino-6-fluoro-5-hydroxy-2-methylbiphenyl-3-carbonitrile (I-41) (300 mg, 1.24 mmol) and N-[(benzyloxy)carbonyl]-N-methylglycine (290 mg, 1.30 mmol), followed by stirring at room temperature for 16 hours. The reaction liquid was concentrated under reduced pressure, dissolved in ethyl acetate, and washed with water and saturated brine. After drying over anhydrous sodium sulfate, the insoluble matter was separated by filtration, the residue obtained by concentration was dissolved in xylene (20 ml), then pyridinium p-toluenesulfonate (120 mg) was added, followed by heating under reflux in an oil bath at 160° C. for 6 hours. The reaction liquid was concentrated under reduced pressure, 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 filtration was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=3:1, v/v) to obtain the entitled compound (242 mg, 46%) as a colorless foamy substance.

後処理

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. dissolutiondissolved in ethyl acetate
  4. washwashed with water and saturated brine
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. customthe insoluble matter was separated by filtration
  7. customthe residue obtained by concentration
  8. temperatureby heating
  9. temperatureunder reflux in an oil bath at 160° C. for 6 hours
  10. customThe reaction liquid
  11. concentrationwas concentrated under reduced pressure
  12. dissolutiondissolved in ethyl acetate
  13. washwashed with saturated brine
  14. dry with materialAfter drying over anhydrous sodium sulfate
  15. customthe insoluble matter was separated by filtration
  16. customthe residue obtained by filtration
  17. customwas purified by silica gel column chromatography (eluent, n-hexane

出典と根拠

ORDレコード
ord-eab524176c6d46468fe70f5a9698e331
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

反応ノート

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