Thionyl Chloride → 6-Chloro-2-fluoro-3-(isobutyramidomethyl)-N-(4-((2,2,2-trifluoroethyl)amino)quinazolin-8-yl)benzamide

HRID 1469859Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1469859
[F:1][C:2]([F:17])([F:16])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[C:10]([NH2:15])[CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][N:6]=1.[Cl:18][C:19]1[C:24]([C:25](O)=[O:26])=[C:23]([F:28])[C:22]([CH2:29][NH:30][C:31](=[O:35])[CH:32]([CH3:34])[CH3:33])=[CH:21][CH:20]=1.S(Cl)(Cl)=O.CCN(C(C)C)C(C)C>C1COCC1>[Cl:18][C:19]1[C:24]([C:25]([NH:15][C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:9]=2[N:8]=[CH:7][N:6]=[C:5]3[NH:4][CH2:3][C:2]([F:1])([F:16])[F:17])=[O:26])=[C:23]([F:28])[C:22]([CH2:29][NH:30][C:31](=[O:35])[CH:32]([CH3:33])[CH3:34])=[CH:21][CH:20]=1

Komponenten

6

Edukt 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 866922656-Chloro-2-fluoro-3-(isobutyramidomethyl)benzoic acidHCID 86692308N4-(2,2,2-trifluoroethyl)quinazoline-4,8-diamine

Produkt 1

HCID 716800586-Chloro-2-fluoro-3-(isobutyramidomethyl)-N-(4-((2,2,2-trifluoroethyl)amino)quinazolin-8-yl)benzamideAusbeute 12,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The title compound was prepared following the procedure described in Example-1 using N4-(2,2,2-trifluoroethyl)quinazoline-4,8-diamine (Intermediate-65, 70 mg, 0.29 mmol), 6-chloro-2-fluoro-3-(isobutyramidomethyl)benzoic acid (Intermediate-60, 118 mg, 0.43 mmol), thionyl chloride (1 mL), and DIPEA (148 mg, 1.15 mmol) in THF (2 mL) to afford 18 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.57 (s, 1H), 8.93 (t, 1H), 8.76-8.73 (d, J=7.2 Hz, 1H), 8.61 (s, 1H), 8.38 (t, 1H), 8.12-8.09 (d, J=9.3 Hz, 1H), 7.66-7.61 (t, J=7.8 Hz, 1H), 7.40-7.38 (m, 2H), 4.47 (m, 2H), 4.32 (d, J=4.8 Hz, 2H), 2.42 (m, 1H), 1.05-1.03 (d, J=6.9 Hz, 6H); MS [M+H]+: 498.31.

Aufarbeitung

  1. customThe title compound was prepared

Quellen und Nachweise

ORD-Eintrag
ord-5bd0ed03764746349e3ca23a6a6685f4
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006257B2

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