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Potassium Carbonate → (3S)-N-ethyl-3-({4-[2-fluoro-4-(7-quinolinyl)phenyl]-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl}methyl)-1-pyrrolidinecarboxamide

HRID 525256
ノート
印刷プレビュー

反応式

HRID 525256 の反応式
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]([NH:22][CH2:23][CH3:24])=[O:21])[CH2:16]2)=[C:4]([F:25])[CH:3]=1.CC1(C)C(C)(C)OB([C:34]2[CH:43]=[C:42]3[C:37]([CH:38]=[CH:39][CH:40]=[N:41]3)=[CH:36][CH:35]=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>[CH2:23]([NH:22][C:20]([N:17]1[CH2:18][CH2:19][C@@H:15]([CH2:14][C:9]2[N:8]([C:5]3[CH:6]=[CH:7][C:2]([C:34]4[CH:43]=[C:42]5[C:37]([CH:38]=[CH:39][CH:40]=[N:41]5)=[CH:36][CH:35]=4)=[CH:3][C:4]=3[F:25])[C:12](=[O:13])[NH:11][N:10]=2)[CH2:16]1)=[O:21])[CH3:24]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 592961167-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)QuinolineHCID 67376184(3S)-3-{[4-(4-bromo-2-fluorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl]methyl}-N-ethyl-1-pyrrolidinecarboxamide

生成物 1

HCID 67375868(3S)-N-ethyl-3-({4-[2-fluoro-4-(7-quinolinyl)phenyl]-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl}methyl)-1-pyrrolidinecarboxamide

試薬・触媒・溶媒 2

HCID 178418807
HCID 178418807、化合物
触媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

A solution of (3S)-3-{[4-(4-bromo-2-fluorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl]methyl}-N-ethyl-1-pyrrolidinecarboxamide (0.179 mmol) in dioxane (2 mL) was treated with 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (0.180 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II)-dichloromethane adduct (15 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 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 (2 mL). All dioxane filtrates were combined and concentrated in vacuo. Reverse phase HPLC (10-70% acetonitrile/water+0.1% NH4OH) was utilized in purifying the title compound (29 mg, 35%). MS(ES)+ m/e 461.2 [M+H]+.

後処理

  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 (2 mL)
  7. concentrationconcentrated in vacuo
  8. customin purifying the title compound (29 mg, 35%)

出典と根拠

ORDレコード
ord-e994dd96e3da4c6eae362a754c06670d
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09340529B2

反応ノート

読み込み中…

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