1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-((R)-3-oxo-1-tosyl-1,2,3,4-tetrahydropyrazin-2-yl)-N-((R)-6-(2-(piperidin-1-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide

HRID 1444723Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1444723
[O:1]=[C:2]1[NH:7][CH:6]=[CH:5][N:4]([S:8]([C:11]2[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[C@@H:3]1[CH2:18][C:19]([OH:21])=O.[N:22]1([CH2:28][CH2:29][C:30]2[CH:31]=[C:32]3[C:37](=[CH:38][CH:39]=2)[C@H:36]([NH2:40])[CH2:35][CH2:34][CH2:33]3)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[O:1]=[C:2]1[NH:7][CH:6]=[CH:5][N:4]([S:8]([C:11]2[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=2)(=[O:9])=[O:10])[C@@H:3]1[CH2:18][C:19]([NH:40][C@H:36]1[C:37]2[C:32](=[CH:31][C:30]([CH2:29][CH2:28][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:39][CH:38]=2)[CH2:33][CH2:34][CH2:35]1)=[O:21]

Komponenten

6

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 58646020(R)-6-(2-(piperidin-1-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-1-amineHCID 59167870(R)-2-(3-oxo-1-tosyl-1,2,3,4-tetrahydropyrazin-2-yl)acetic acid

Produkt 1

HCID 686789922-((R)-3-oxo-1-tosyl-1,2,3,4-tetrahydropyrazin-2-yl)-N-((R)-6-(2-(piperidin-1-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of (R)-2-(3-oxo-1-tosyl-1,2,3,4-tetrahydropyrazin-2-yl)acetic acid (310 mg, 1.0 mmol), crude (R)-6-(2-(piperidin-1-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-1-amine (310 mg, 1.2 mmol), HOBt (135 mg, 1.0 mmol) and EDCI (191 mg, 1.0 mmol) in 1 mL of DMF was stirred overnight at room temperature. After quenching with sat. NaHCO3 solution, the reaction mixture was extracted with EtOAc. The combined organic phase was washed brine, dried over Na2SO4, and evaporated in vacuo. Flash chomatography (SiO2, EtOAc/MeOH=100:15 to 100:20 to EtOAc/2.0M NH3 in MeOH=100:10 to 100:15 to 100:20 ) gave the desired product as a white solid. MS: 551.2 (M+1).

Aufarbeitung

  1. customAfter quenching with sat. NaHCO3 solution
  2. extractionthe reaction mixture was extracted with EtOAc
  3. washThe combined organic phase was washed brine
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-70c3718e202840e3ab8cb749f359385f
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07662811B2

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