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

HRID 1469863Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1469863
[CH:1]([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)([CH3:3])[CH3:2].[Cl:16][C:17]1[C:22]([C:23](O)=[O:24])=[C:21]([F:26])[C:20]([CH2:27][NH:28][C:29](=[O:33])[CH:30]([CH3:32])[CH3:31])=[CH:19][CH:18]=1.S(Cl)(Cl)=O.CCN(C(C)C)C(C)C>C1COCC1>[Cl:16][C:17]1[C:22]([C:23]([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][CH:1]([CH3:3])[CH3:2])=[O:24])=[C:21]([F:26])[C:20]([CH2:27][NH:28][C:29](=[O:33])[CH:30]([CH3:31])[CH3:32])=[CH:19][CH:18]=1

Komponenten

6

Edukt 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 866922656-Chloro-2-fluoro-3-(isobutyramidomethyl)benzoic acidHCID 86692303N4-isopropylquinazoline-4,8-diamine

Produkt 1

HCID 716802296-Chloro-2-fluoro-3-(isobutyramidomethyl)-N-(4-(isopropylamino)quinazolin-8-yl)benzamideAusbeute 17,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The title compound was prepared following the procedure described in Example-1 using N4-isopropylquinazoline-4,8-diamine (Intermediate-57, 50 mg, 0.25 mmol), 6-chloro-2-fluoro-3-(isobutyramidomethyl)benzoic acid (Intermediate-60, 100 mg, 0.37 mmol), thionyl chloride (1 mL), and DIPEA (127 mg, 0.99 mmol) in THF (2 mL) to afford 20 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.42 (s, 1H), 8.70-8.67 (d, J=7.2 Hz, 1H), 8.48 (s, 1H), 8.37 (t, 1H), 8.11-8.08 (d, J=7.8 Hz, 2H), 7.53 (t, 1H), 7.41 (m, 2H), 4.55 (m, 1H), 4.31 (d, 2H), 2.50 (m, 1H), 1.27 (d, J=6.6 Hz, 6H), 1.05-1.03 (d, J=6.9 Hz, 6H); MS [M+H]+: 458.47.

Aufarbeitung

  1. customThe title compound was prepared

Quellen und Nachweise

ORD-Eintrag
ord-6b175323b57c4034b7b2f0872ce9c875
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006257B2

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