Triethylamine → 2-(3-fluoropyridin-2-yl)-5-{(9-methoxy-3,4-dihydro-2Hbenzo[b][1,4]dioxepin-7-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-2,4-dihydro-[1,1,4]triazol-3-one

HRID 1698681노트

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HRID 1698681 반응식
[F:1][C:2]1[C:3](NN)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:10]([N:12](CC)CC)C.CO[C:19](=[O:51])[N:20]=[C:21](SC)[C:22]([C:36]1[CH:46]=[C:45]([O:47][CH3:48])[C:39]2[O:40][CH2:41][CH2:42][CH2:43][O:44][C:38]=2[CH:37]=1)=[N:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[N:34]=[C:33]([CH3:35])[O:32][N:31]=2)=[CH:26][CH:25]=1>CN(C=O)C>[F:1][C:2]1[C:3]([CH:10]2[C:19](=[O:51])[NH:20][C:21]([CH:22]([C:36]3[CH:46]=[C:45]([O:47][CH3:48])[C:39]4[O:40][CH2:41][CH2:42][CH2:43][O:44][C:38]=4[CH:37]=3)[NH:23][C:24]3[CH:25]=[CH:26][C:27]([C:30]4[N:34]=[C:33]([CH3:35])[O:32][N:31]=4)=[CH:28][CH:29]=3)=[N:12]2)=[N:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 269852863-Fluoro-2-hydrazinylpyridineHCID 72312720[2-(9-methoxy-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene]carbamic acid methyl ester

생성물 1

HCID 670970522-(3-fluoropyridin-2-yl)-5-{(9-methoxy-3,4-dihydro-2Hbenzo[b][1,4]dioxepin-7-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-2,4-dihydro-[1,1,4]triazol-3-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
85 °C

실험 절차

After adding 28 mg of (3-fluoropyridin-2-yl)hydrazine and 50 μl of triethylamine to a solution of 119 mg of {2-(9-methoxy-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester in 2 ml of DMF, the mixture was stirred overnight at 85° C. under a nitrogen atmosphere. The reaction mixture was concentrated, and the residue was dissolved in 3 ml of methanol and 0.3 ml of acetic acid. After adding 100 mg of sodium cyanotrihydroborate to the reaction mixture, it was stirred at room temperature for 1 hour. Water was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by NAM silica gel column chromatography (methanol-ethyl acetate) to give 2-(3-fluoropyridin-2-yl)-5-{(9-methoxy-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-2,4-dihydro-[1,1,4]triazol-3-one.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in 3 ml of methanol
  3. additionAfter adding 100 mg of sodium cyanotrihydroborate to the reaction mixture, it
  4. stirringwas stirred at room temperature for 1 hour
  5. additionWater was added to the reaction mixture and extraction
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationThe desiccating agent was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by NAM silica gel column chromatography (methanol-ethyl acetate)

출처 및 근거

ORD 기록
ord-55f8fea4ba1743cd9614d1d4863c577e
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163787B2

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