Potassium Carbonate → 5-{[(3S)-1-acetyl-3-pyrrolidinyl]methyl}-4-[4-(7-quinolinyl)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 525241노트

반응식

HRID 525241 반응식
[C:1]([N:4]1[CH2:8][CH2:7][C@@H:6]([CH2:9][C:10]2[N:11]([C:16]3[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=3)[C:12](=[O:15])[NH:13][N:14]=2)[CH2:5]1)(=[O:3])[CH3:2].CC1(C)C(C)(C)OB([C:31]2[CH:40]=[C:39]3[C:34]([CH:35]=[CH:36][CH:37]=[N:38]3)=[CH:33][CH:32]=2)O1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[C:1]([N:4]1[CH2:8][CH2:7][C@@H:6]([CH2:9][C:10]2[N:11]([C:16]3[CH:21]=[CH:20][C:19]([C:31]4[CH:40]=[C:39]5[C:34]([CH:35]=[CH:36][CH:37]=[N:38]5)=[CH:33][CH:32]=4)=[CH:18][CH:17]=3)[C:12](=[O:15])[NH:13][N:14]=2)[CH2:5]1)(=[O:3])[CH3:2]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 592961167-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)QuinolineHCID 673757745-{[(3S)-1-acetyl-3-pyrrolidinyl]methyl}-4-(4-bromophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

생성물 1

HCID 673540705-{[(3S)-1-acetyl-3-pyrrolidinyl]methyl}-4-[4-(7-quinolinyl)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

시약·촉매·용매 2

HCID 178418807HCID 178418807, 화합물촉매HCID 312751,4-Dioxane용매

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온도
110 °C

실험 절차

A solution of 5-{[(3S)-1-acetyl-3-pyrrolidinyl]methyl}-4-(4-bromophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (0.211 mmol) in dioxane (2 mL) was treated with 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (0.216 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II)-dichloromethane adduct (20 mg), and 2M aq potassium carbonate (1 mL). The reaction mixture was purged with nitrogen, sealed, and stirred at 110° C. for 1 h. The reaction mixture was cooled to room temperature, diluted with water, neutralized with the dropwise addition of 6N aq HCl, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Reverse phase HPLC (10-70% acetonitrile/water+0.1% NH4OH) was utilized to purify the title compound (29 mg, 33%). MS(ES)+ m/e 413.8 [M+H]+.

후처리

  1. customThe reaction mixture was purged with nitrogen
  2. customsealed
  3. temperatureThe reaction mixture was cooled to room temperature
  4. additiondiluted with water
  5. additionneutralized with the dropwise addition of 6N aq HCl
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto purify the title compound (29 mg, 33%)

출처 및 근거

ORD 기록
ord-4452e4332bdd4271a4ea93e76ded4053
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340529B2

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