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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Potassium Carbonate → 1,1-dimethylethyl (3S)-3-({5-oxo-4-[4-(7-quinolinyl)phenyl]-4,5-dihydro-1H-1,2,4-triazol-3-yl}methyl)-1-pyrrolidinecarboxylate

HRID 525257
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HRID 525257 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[NH:11][N:10]=[C:9]2[CH2:14][C@@H:15]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16]2)=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:35]2[CH:44]=[C:43]3[C:38]([CH:39]=[CH:40][CH:41]=[N:42]3)=[CH:37][CH:36]=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>[O:13]=[C:12]1[NH:11][N:10]=[C:9]([CH2:14][C@@H:15]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16]2)[N:8]1[C:5]1[CH:6]=[CH:7][C:2]([C:35]2[CH:44]=[C:43]3[C:38]([CH:39]=[CH:40][CH:41]=[N:42]3)=[CH:37][CH:36]=2)=[CH:3][CH:4]=1
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 592961167-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)QuinolineHCID 673758331,1-dimethylethyl (3S)-3-{[4-(4-bromophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl]methyl}-1-pyrrolidinecarboxylate

생성물 1

HCID 673769061,1-dimethylethyl (3S)-3-({5-oxo-4-[4-(7-quinolinyl)phenyl]-4,5-dihydro-1H-1,2,4-triazol-3-yl}methyl)-1-pyrrolidinecarboxylate

시약·촉매·용매 2

HCID 178418807
HCID 178418807, 화합물
촉매
HCID 312751,4-Dioxane용매

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온도
110 °C

실험 절차

A solution of 1,1-dimethylethyl (3S)-3-{[4-(4-bromophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl]methyl}-1-pyrrolidinecarboxylate (1.181 mmol) in dioxane (6 mL) was treated with 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (1.215 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II)-dichloromethane adduct (50 mg), and 2M aq potassium carbonate (3 mL). The reaction mixture was purged with nitrogen, sealed, and stirred at 110° C. for 1 h. The solution was cooled to room temperature and the dioxane layer separated from the aqueous layer. The dioxane layer was removed via pipette and was passed through a plug of celite and sodium sulfate. The plug was washed with dioxane (6 mL). All dioxane filtrates were combined and concentrated in vacuo. Silica gel chromatography (0-20% methanol:ethyl acetate) was utilized in purifying the title compound (386 mg, 69%). MS(ES)+ m/e 472.2 [M+H]+.

후처리

  1. customThe reaction mixture was purged with nitrogen
  2. customsealed
  3. temperatureThe solution was cooled to room temperature
  4. customthe dioxane layer separated from the aqueous layer
  5. customThe dioxane layer was removed via pipette
  6. washThe plug was washed with dioxane (6 mL)
  7. concentrationconcentrated in vacuo
  8. customin purifying the title compound (386 mg, 69%)

출처 및 근거

ORD 기록
ord-5372aec1464d4f2490bb297f035542e2
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09340529B2

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