1,2-Dichloroethane → 3-(3-fluoropyridin-2-yl)-N-[(1R)-1-(5-fluoropyridin-2-yl)ethyl]-5-(5-methylpyridin-2-yl)benzamide

HRID 888394Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 888394
[Cl-].[Na+].[F:3][C:4]1[C:5]([C:10]2[CH:11]=[C:12]([CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=3)[CH:18]=2)[C:13]([OH:15])=O)=[N:6][CH:7]=[CH:8][CH:9]=1.Cl.[F:27][C:28]1[CH:29]=[CH:30][C:31]([C@H:34]([NH2:36])[CH3:35])=[N:32][CH:33]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C)C=O>[F:3][C:4]1[C:5]([C:10]2[CH:11]=[C:12]([CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=3)[CH:18]=2)[C:13]([NH:36][C@@H:34]([C:31]2[CH:30]=[CH:29][C:28]([F:27])=[CH:33][N:32]=2)[CH3:35])=[O:15])=[N:6][CH:7]=[CH:8][CH:9]=1

Komponenten

8

Edukt 6

HCID 111,2-DichloroethaneHCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 66690953(1R)-1-(5-fluoropyridin-2-yl)ethan-1-amine hydrochlorideHCID 684966373-(3-Fluoropyridin-2-yl)-5-(5-methylpyridin-2-yl)benzoic acid

Produkt 1

HCID 252567493-(3-fluoropyridin-2-yl)-N-[(1R)-1-(5-fluoropyridin-2-yl)ethyl]-5-(5-methylpyridin-2-yl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of the sodium chloride salt of 3-(3-fluoropyridin-2-yl)-5-(5-methylpyridin-2-yl)benzoic acid (25.0 mg, 0.05 mmol) in N,N-dimethylformamide (0.35 mL) were added (1R)-1-(5-fluoropyridin-2-yl)ethanamine hydrochloride salt (16.5 mg, 0.08 mmol), EDC (14.9 mg, 0.08 mmol), HOBT (7.92 mg, 0.05 mmol) and triethylamine (21.6 μL, 0.16 mmol). The reaction mixture was stirred at ambient temperature. After 18 h, the mixture was cooled to ambient temperature. Purification by reverse phase HPLC (C-18, 95% water/acetonitrile→50% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound. HRMS 431.1706 (M+1). 1H NMR (500 MHz, CDCl3): δ 8.73 (q, J=1.6 Hz, 1H); 8.57-8.54 (m, 2H); 8.52 (t, J=1.7 Hz, 1H); 8.45 (q, J=1.5 Hz, 1H); 8.44 (d, J=2.8 Hz, 1H); 7.78 (d, J=8.1 Hz, 1H); 7.62-7.52 (m, 3H); 7.43-7.31 (m, 3H); 5.43 (p, J=7.0 Hz, 1H); 2.40 (s, 3H); 1.61 (d, J=6.8 Hz, 3H).

Aufarbeitung

  1. temperaturethe mixture was cooled to ambient temperature
  2. customPurification by reverse phase HPLC (C-18, 95% water/acetonitrile→50% water/acetonitrile with 0.1% trifluoroacetic acid)

Quellen und Nachweise

ORD-Eintrag
ord-65f3273bed1647e9938f50ca54aad221
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247401B2

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