1-Hydroxybenzotriazole → (2E)-3-(4-Chlorophenyl)-N-[(1S)-2-[(2-{4-[(3,5-dichloro-2-pyridyl)oxy]-1-piperidinyl}-2-oxoethyl)amino]-2-oxo-1-(2-pyridylmethyl)ethyl]-2-propenamide

HRID 1246756

Reaktionsgleichung

Reaktionsgleichung von HRID 1246756
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([NH:12][C@@H:13]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[C:14]([NH:16][CH2:17][C:18]([OH:20])=O)=[O:15])=[O:11])=[CH:4][CH:3]=1.Cl.Cl.[Cl:30][C:31]1[C:32]([O:38][CH:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)=[N:33][CH:34]=[C:35]([Cl:37])[CH:36]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([NH:12][C@@H:13]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[C:14]([NH:16][CH2:17][C:18]([N:42]2[CH2:43][CH2:44][CH:39]([O:38][C:32]3[C:31]([Cl:30])=[CH:36][C:35]([Cl:37])=[CH:34][N:33]=3)[CH2:40][CH2:41]2)=[O:20])=[O:15])=[O:11])=[CH:6][CH:7]=1

Komponenten

7

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 219060913,5-Dichloro-2-(4-piperidinyloxy)pyridine dihydrochlorideHCID 69379045[[(2S)-2-[[(2E)-3-(4-Chlorophenyl)-2-propenoyl]amino]-3-(2-pyridyl)propanoyl]amino]acetic acid

Produkt 1

HCID 69379614(2E)-3-(4-Chlorophenyl)-N-[(1S)-2-[(2-{4-[(3,5-dichloro-2-pyridyl)oxy]-1-piperidinyl}-2-oxoethyl)amino]-2-oxo-1-(2-pyridylmethyl)ethyl]-2-propenamideAusbeute 76,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of {[(2S)-2-{[(2E)-3-(4-chlorophenyl)-2-propenoyl]amino}-3-(2-pyridyl)propanoyl]amino}acetic acid (0.19 g), 3,5-dichloro-2-(4-piperidinyloxy)pyridine dihydrochloride (0.16 g), 1-hydroxybenzotriazole (0.084 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.11 g) in N,N-dimethylformamide (2.5 ml) was added dropwise N,N-diisopropylethylamine (0.27 ml) at 8° C. The mixture was warmed to room temperature and stirred for 6 hours. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography to give the title compound (231 mg).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ea858edac1a64b4083b1cfca2779459a
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129243B2

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