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

HRID 17559

반응식

HRID 17559 반응식
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]

참가 물질

9

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 7237O-Xylene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-eab524176c6d46468fe70f5a9698e331
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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