1,2-Dichloroethane → {1-[(1-Benzyl-5-hydroxy-2-oxo-3-phenyl-8-pyridin-3-yl-1,2-dihydro-[1,7]naphthyridine-6-carbonyl)-amino]-cyclopropyl}-acetic acid methyl ester

HRID 920106Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 920106
[CH2:1]([N:8]1[C:17]2[C:12](=[C:13]([OH:27])[C:14]([C:24](O)=[O:25])=[N:15][C:16]=2[C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:11]=[C:10]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:9]1=[O:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.Cl.[CH3:50][O:51][C:52](=[O:58])[CH2:53][C:54]1([NH2:57])[CH2:56][CH2:55]1.CCN(C(C)C)C(C)C>C(Cl)Cl.CCOC(C)=O>[CH3:50][O:51][C:52](=[O:58])[CH2:53][C:54]1([NH:57][C:24]([C:14]2[C:13]([OH:27])=[C:12]3[C:17](=[C:16]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)[N:15]=2)[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9](=[O:34])[C:10]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[CH:11]3)=[O:25])[CH2:56][CH2:55]1

Komponenten

8

Edukt 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57350660Methyl 2-(1-aminocyclopropyl)acetate hydrochlorideHCID 682974401-Benzyl-5-hydroxy-2-oxo-3-phenyl-8-pyridin-3-yl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid

Produkt 1

HCID 68297247{1-[(1-Benzyl-5-hydroxy-2-oxo-3-phenyl-8-pyridin-3-yl-1,2-dihydro-[1,7]naphthyridine-6-carbonyl)-amino]-cyclopropyl}-acetic acid methyl esterAusbeute 5,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 1-benzyl-5-hydroxy-2-oxo-3-phenyl-8-pyridin-3-yl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid (68 mg, 0.15 mmol) and HOBt (33 mg, 0.24 mmol) was dissolved in CH2Cl2 (3 mL). EDC (52 mg, 0.27 mmol) was added, and the resulting mixture was stirred for 10 min. (1-Amino-cyclopropyl)-acetic acid methyl ester HCl salt (40 mg, 0.24 mmol) and Hunig's base (0.1 mL, 0.55 mmol) were added, and the mixture was stirred for 16 h. The mixture was diluted with EtOAc and washed with 0.1 M HCl. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by silica gel chromatography (5-90% EtOAc/hexanes+1% AcOH) to give 5 mg of the title compound as a yellow solid. MS: (+) m/z 561.34 (M+1).

Aufarbeitung

  1. additionwere added
  2. washwashed with 0.1 M HCl
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel chromatography (5-90% EtOAc/hexanes+1% AcOH)

Quellen und Nachweise

ORD-Eintrag
ord-00c1fbfdb5f64ab1a0b980724138d0e4
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09271970B2

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