Triethylamine → 2-(3-Fluoro-pyridin-2-yl)-5-{(8-methoxychroman-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-2,4-dihydro-[1,2,4]triazol-3-one

HRID 1161428노트

반응식

HRID 1161428 반응식
[F:1][C:2]1[C:3]([NH:8][NH2:9])=[N:4][CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.C[O:18][C:19](=O)[N:20]=[C:21](SC)[C:22]([C:36]1[CH:37]=[C:38]2[C:43](=[C:44]([O:46][CH3:47])[CH:45]=1)[O:42][CH2:41][CH2:40][CH2:39]2)=[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]([N:8]2[C:19](=[O:18])[NH:20][C:21]([CH:22]([C:36]3[CH:37]=[C:38]4[C:43](=[C:44]([O:46][CH3:47])[CH:45]=3)[O:42][CH2:41][CH2:40][CH2:39]4)[NH:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]4[N:34]=[C:33]([CH3:35])[O:32][N:31]=4)=[CH:26][CH:25]=3)=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 269852863-Fluoro-2-hydrazinylpyridineHCID 72312814{2-(8-Methoxychroman-6-yl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester

생성물 1

HCID 1363663282-(3-Fluoro-pyridin-2-yl)-5-{(8-methoxychroman-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-2,4-dihydro-[1,2,4]triazol-3-one수율 57.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
85 °C

실험 절차

After adding 25 mg of (3-fluoropyridin-2-yl)hydrazine and 50 μl of triethylamine to a solution of 100 mg of {2-(8-methoxychroman-6-yl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester (Example (24a)) 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 2 hours. 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-fluoro-pyridin-2-yl)-5-{(8-methoxychroman-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-2,4-dihydro-[1,2,4]triazol-3-one (60 mg).

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 2 hours
  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-180e349f488146f998ce76f923196420
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816522B2

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