Sodium Chloride → 2-Tert-butyl-7-(4-fluorophenyl)-N-{(1R)-1-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl}-1,3-benzoxazole-5-carboxamide

HRID 592313

Reaktionsgleichung

Reaktionsgleichung von HRID 592313
[C:1]([C:5]1[O:6][C:7]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[CH:12][C:11]([C:21](O)=[O:22])=[CH:10][C:8]=2[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[Na+].Cl.Cl.[F:28][C:29]([F:40])([F:39])[C:30]1[N:35]=[CH:34][C:33]([C@H:36]([NH2:38])[CH3:37])=[CH:32][N:31]=1.CN1CCOCC1.Cl.CN(C)CCN=C=NCC.ON1C2N=CC=CC=2N=N1>CN(C)C=O>[C:1]([C:5]1[O:6][C:7]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[CH:12][C:11]([C:21]([NH:38][C@@H:36]([C:33]3[CH:32]=[N:31][C:30]([C:29]([F:40])([F:39])[F:28])=[N:35][CH:34]=3)[CH3:37])=[O:22])=[CH:10][C:8]=2[N:9]=1)([CH3:2])([CH3:3])[CH3:4]

Komponenten

8

Edukt 6

HCID 5234Sodium ChlorideHCID 79724-MethylmorpholineHCID 181649HOAtHCID 57494384N-[2-(dimethylamino)ethyl]-N'-ethylcarbodiimide hydrochlorideHCID 66689953HCID 66689953, VerbindungHCID 66690185HCID 66690185, Verbindung

Produkt 1

HCID 469170242-Tert-butyl-7-(4-fluorophenyl)-N-{(1R)-1-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl}-1,3-benzoxazole-5-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of 2-tert-butyl-7-(4-fluorophenyl)-1,3-benzoxazole-5-carboxylic acid with three equivalents of sodium chloride (30 mg, 74.0 μmol), (1R)-1-[2-(trifluoromethyl)pyrimidin-5-yl]ethanamine dihydrochloride (19.5 mg, 74.0 μmol) and N-methylmorpholine (33.7 μL, 0.307 mmol) in N,N-dimethylformamide (0.409 mL) were added N[2-(dimethylamino)ethyl]-N′-ethylcarbodiimide hydrochloride (20.6 mg, 107 μmol), 1-hydroxy-7-azabenzotriazole (4.2 mg, 31.0 μmol). The mixture was stirred at 40° C. for 1 h. Purification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.05% ammonium hydroxide) gave the title compound (22.6 mg). HRMS [M+1] found=487.1766. 1H NMR (500 MHz, DMSO-d 6): δ 9.15 (2H, s), 8.20 (1H, s), 8.14 (1H, s), 8.02 (2H, t, J=6.70 Hz), 7.45 (2H, t, J=8.65 Hz), 5.33 (1H, m, J=7.09 Hz), 1.63 (3H, d, J=7.07 Hz), 1.47 (9H, s).

Aufarbeitung

  1. customPurification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.05% ammonium hydroxide)

Quellen und Nachweise

ORD-Eintrag
ord-184cb5ad98654510ac41e8a7535c2b8b
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238647B2

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