Triethylamine → 1-{2-Oxo-2-[4-(4-pyrimidin-2-yl-phenyl)-piperazin-1-yl]-ethyl}-pyrrolidine-3-carboxylic acid methyl ester

HRID 1037984Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1037984
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:19][O:20][C:21]([CH:23]1[CH2:27][CH2:26][N:25]([CH2:28][C:29](O)=[O:30])[CH2:24]1)=[O:22].C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[CH3:19][O:20][C:21]([CH:23]1[CH2:27][CH2:26][N:25]([CH2:28][C:29](=[O:30])[N:4]2[CH2:5][CH2:6][N:1]([C:7]3[CH:12]=[CH:11][C:10]([C:13]4[N:14]=[CH:15][CH:16]=[CH:17][N:18]=4)=[CH:9][CH:8]=3)[CH2:2][CH2:3]2)[CH2:24]1)=[O:22]

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 534203192-(4-(Piperazin-1-yl)phenyl)pyrimidine2×HCID 674208411-Carboxymethyl-pyrrolidine-3-carboxylic acid methyl ester2×

Produkt 1

HCID 674190531-{2-Oxo-2-[4-(4-pyrimidin-2-yl-phenyl)-piperazin-1-yl]-ethyl}-pyrrolidine-3-carboxylic acid methyl esterAusbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-(4-piperazin-1-yl-phenyl)-pyrimidine (compound 10 from Step 7, 14.7 mmol) and 1-Carboxymethyl-pyrrolidine-3-carboxylic acid methyl ester (compound 5 from Step 3, 17.6 mmol) were dissolved in 72 ml of DMF. Triethylamine (8 ml, 57 mmol), 1-hydroxybenztriazole (2.29 gm) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCl) (3.43 gm, 18 mmol) were added and the reaction mixture stirred for 24 hrs. After washing with brine, extracting with dichloromethane, and drying over magnesium sulfate, the mixture was evaporated and chromatographed on silica gel to obtain 5.0 gm of title product.

Aufarbeitung

  1. washAfter washing with brine
  2. extractionextracting with dichloromethane
  3. dry with materialdrying over magnesium sulfate
  4. customthe mixture was evaporated
  5. customchromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f500272d170e45e2b7ea02e06a48716c
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546404B2

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