Azetidine → [2-(5-{1-[4-(azetidin-1-ylcarbonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3-thiazol-5-yl]methanol

HRID 1881997Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1881997
[OH:1][CH2:2][C:3]1[S:7][C:6]([C:8]2[NH:12][C:11]([CH:13]([C:21]3[CH:29]=[CH:28][C:24]([C:25]([OH:27])=O)=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:10][CH:9]=2)=[N:5][CH:4]=1.Cl.C(N=C=NC[CH2:37][CH2:38][N:39]([CH3:41])C)C.ON1C2C=CC=CC=2N=N1.N1CCC1>CN(C)C=O.C(OCC)(=O)C>[N:39]1([C:25]([C:24]2[CH:28]=[CH:29][C:21]([CH:13]([C:11]3[NH:12][C:8]([C:6]4[S:7][C:3]([CH2:2][OH:1])=[CH:4][N:5]=4)=[CH:9][CH:10]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:22][CH:23]=2)=[O:27])[CH2:38][CH2:37][CH2:41]1

Komponenten

7

Edukt 4

HCID 10422AzetidineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 593312214-[1-{5-[5-(hydroxymethyl)-1,3-thiazol-2-yl]-1H-pyrrol-2-yl}-2-(tetrahydro-2H-pyran-4-yl)ethyl]benzoic acid

Produkt 1

HCID 59331308[2-(5-{1-[4-(azetidin-1-ylcarbonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3-thiazol-5-yl]methanolAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-[1-{5-[5-(hydroxymethyl)-1,3-thiazol-2-yl]-1H-pyrrol-2-yl}-2-(tetrahydro-2H-pyran-4-yl)ethyl]benzoic acid (100 mg) in N,N-dimethylformamide (5 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (70.0 mg) and 1-hydroxybenzotriazole (50.0 mg), and the mixture was stirred for 30 min. To the reaction mixture was added azetidine (21.0 mg), and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate and washed with 1M hydrochloric acid. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (30.0 mg, yield 28%) was obtained as a colorless amorphous solid from a fraction eluted with ethyl acetate-methanol (9:1, volume ratio). MS: 452 (MH+).

Aufarbeitung

  1. stirringthe mixture was stirred overnight at room temperature
  2. washwashed with 1M hydrochloric acid
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-372e500fcf4044289fef584d749a6989
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318746B2

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