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

HRID 525243
ノート
印刷プレビュー

反応式

HRID 525243 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13][C@@H:14]3[CH2:18][CH2:17][N:16]([C:19](=[O:22])[CH2:20][CH3:21])[CH2:15]3)=[N:11][NH:10][C:9]2=[O:23])=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:32]2[CH:41]=[C:40]3[C:35]([CH:36]=[CH:37][CH:38]=[N:39]3)=[CH:34][CH:33]=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:19]([N:16]1[CH2:17][CH2:18][C@@H:14]([CH2:13][C:12]2[N:8]([C:5]3[CH:6]=[CH:7][C:2]([C:32]4[CH:41]=[C:40]5[C:35]([CH:36]=[CH:37][CH:38]=[N:39]5)=[CH:34][CH:33]=4)=[CH:3][CH:4]=3)[C:9](=[O:23])[NH:10][N:11]=2)[CH2:15]1)(=[O:22])[CH2:20][CH3:21]
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 673773044-(4-bromophenyl)-5-{[(3S)-1-propanoyl-3-pyrrolidinyl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one

生成物 1

HCID 673556125-{[(3S)-1-propanoyl-3-pyrrolidinyl]methyl}-4-[4-(7-quinolinyl)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

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 4-(4-bromophenyl)-5-{[(3S)-1-propanoyl-3-pyrrolidinyl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one (0.171 mmol) in dioxane (2 mL) was treated with 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (0.176 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 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 (44 mg, 59%). MS(ES)+ m/e 427.8 [M+H]+.

後処理

  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 (44 mg, 59%)

出典と根拠

ORDレコード
ord-acf3748e93314af186c912dbc63930b0
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…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート