Diisopropylethylamine → 2-[1-(4-dimethylaminomethyl-benzoyl)piperidin-4-yloxy]-1-methyl-1H-[4,4']bipyrimidinyl-6-one

HRID 1468786

Reaktionsgleichung

Reaktionsgleichung von HRID 1468786
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][N:10]=2)[N:4]=[C:3]1[O:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.[CH3:22][N:23]([CH2:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][CH:27]=1)[CH3:24].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH3:24][N:23]([CH2:25][C:26]1[CH:27]=[CH:28][C:29]([C:30]([N:19]2[CH2:20][CH2:21][CH:16]([O:15][C:3]3[N:2]([CH3:1])[C:7](=[O:8])[CH:6]=[C:5]([C:9]4[CH:14]=[CH:13][N:12]=[CH:11][N:10]=4)[N:4]=3)[CH2:17][CH2:18]2)=[O:31])=[CH:33][CH:34]=1)[CH3:22]

Komponenten

7

Edukt 5

HCID 81531DiisopropylethylamineHCID 8263194-[(Dimethylamino)methyl]benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 679776501-methyl-2-(piperidin-4-yloxy)-1H-[4,4']bipyrimidinyl-6-one

Produkt 1

HCID 679776882-[1-(4-dimethylaminomethyl-benzoyl)piperidin-4-yloxy]-1-methyl-1H-[4,4']bipyrimidinyl-6-oneAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 1-methyl-2-(piperidin-4-yloxy)-1H-[4,4′]bipyrimidinyl-6-one (290 mg, 1.0 mmol), 4-dimethylaminomethyl benzoic acid (180 mg, 1.0 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (380 mg, 2.0 mmol) and 1-hydroxybenzotriazole monohydrate (310 mg, 2.0 mmol) in N,N-dimethylformamide (10 ml) was added N,N-diisopropylethylamine (130 mg, 1.0 mmol) at room temperature. The mixture was stirred at room temperature for 3 hours. The mixture was partitioned between water and dichloromethane. The organic layer was washed with water (three times), dried over sodium sulfate, and concentrated in vacuo. The residue was purified by NH-silica gel column chromatography (eluent; hexane/ethyl acetate=15/85) to afford 2-[1-(4-dimethylaminomethyl-benzoyl)piperidin-4-yloxy]-1-methyl-1H-[4,4′]bipyrimidinyl-6-one as a colorless solid (66 mg, 0.15 mmol, 15%).

Aufarbeitung

  1. customThe mixture was partitioned between water and dichloromethane
  2. washThe organic layer was washed with water (three times)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by NH-silica gel column chromatography (eluent; hexane/ethyl acetate=15/85)

Quellen und Nachweise

ORD-Eintrag
ord-819aea120ff84d509a8ebc70598cd722
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006232B2

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