Cesium carbonate → 3-(4-Tert-butylphenyl)-5,5-dimethyl-1-[(2-{[4-(pyrrolidin-1-ylmethyl)phenyl]amino}pyridin-4-yl)methyl]imidazolidine-2,4-dione

HRID 546613

반응식

HRID 546613 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[N:13]([CH2:19][C:20]3[CH:25]=[CH:24][N:23]=[C:22](Cl)[CH:21]=3)[C:12]2=[O:27])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[N:28]1([CH2:33][C:34]2[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=2)[CH2:32][CH2:31][CH2:30][CH2:29]1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C=CC(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=2OC2C1=CC=C(P(C1C=CC=CC=1)C1C=CC=CC=1)C=2>O1CCOCC1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[N:13]([CH2:19][C:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH:38][C:37]4[CH:36]=[CH:35][C:34]([CH2:33][N:28]5[CH2:32][CH2:31][CH2:30][CH2:29]5)=[CH:40][CH:39]=4)[CH:21]=3)[C:12]2=[O:27])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 7768524-(Pyrrolidin-1-ylmethyl)anilineHCID 576259713-(4-Tert-butylphenyl)-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dioneHCID 86628973(9,9-dimethyl-9H-xanthene-3,6-diyl)bis(diphenylphosphine)

생성물 1

HCID 576260133-(4-Tert-butylphenyl)-5,5-dimethyl-1-[(2-{[4-(pyrrolidin-1-ylmethyl)phenyl]amino}pyridin-4-yl)methyl]imidazolidine-2,4-dione수율 5.7%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

To a solution of 1.15 g of 3-(4-tert-butylphenyl)-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dione obtained in stage a) of Example 7 in 50 mL of dioxane are successively added, under argon, 520 mg of 4-(pyrrolidin-1-ylmethyl)aniline obtained in stage c) below, 3.4 g of caesium carbonate, 207 mg of (9,9-dimethyl-9H-xanthene-3,6-diyl)bis(diphenylphosphine) [xantphos] and 67 mg of palladium diacetate. The reaction mixture is heated at 90° C. for 6 hours, filtered and concentrated under reduced pressure. The residue is purified by chromatography on a column of silica, eluting with a mixture of dichloromethane and methanol (90/10 by volume) to give 88 mg of 3-(4-tert-butylphenyl)-5,5-dimethyl-1-[(2-{[4-(pyrrolidin-1-ylmethyl)phenyl]amino}pyridin-4-yl)methyl]imidazolidine-2,4-dione, the characteristics of which are as follows:

후처리

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. customThe residue is purified by chromatography on a column of silica
  4. washeluting with a mixture of dichloromethane and methanol (90/10 by volume)

출처 및 근거

ORD 기록
ord-16fbfdfd7e1f496eb97bd79b9f8bcfb9
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935819B2

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