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Dimethylformamide → HCID 69519057, Verbindung

HRID 1373371
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1373371
CN(C=O)C.[C:6]([O:10][C:11](=[O:29])[NH:12][C@H:13]([C:17]1[NH:26][C:25](=[O:27])[C:24]2[C:19](=[CH:20][C:21]([Cl:28])=[CH:22][CH:23]=2)[N:18]=1)[CH:14]([CH3:16])[CH3:15])([CH3:9])([CH3:8])[CH3:7].[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(=O)([O-])[O-].[K+].[K+]>O>[C:6]([O:10][C:11](=[O:29])[NH:12][C@H:13]([C:17]1[N:26]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25](=[O:27])[C:24]2[C:19](=[CH:20][C:21]([Cl:28])=[CH:22][CH:23]=2)[N:18]=1)[CH:14]([CH3:16])[CH3:15])([CH3:8])([CH3:9])[CH3:7]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 136376396HCID 136376396, Verbindung

Produkt 1

HCID 69519057HCID 69519057, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962Water
Lösungsmittel

Versuchsvorschrift

A dry 3-necked, round bottomed flask, equipped with a magnetic stirrer and nitrogen inlet, was charged with 50 mL of DMF, 3.50 g (10 mmol) of (S)-[1-(7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methylpropyl]-carbamic acid tert-butyl ester (the compound of Formula 202 prepared, e.g., as described in Example 3.2), 1.34 mL of benzyl bromide (98%), and 3.04 g of potassium carbonate. The mixture was stirred at room temperature overnight. TLC (hexanes/ethyl acetate 7:3) indicated complete reaction. The mixture was transferred into a Erlenmeyer flask and mixed with 100 mL of water. To the stirring mixture was then added hexanes, 50 mL. The formed white solid was collected by filtration to afford the title compound of Formula 203 (S)-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methylpropyl]-carbamic acid tert-butyl ester (also corresponding to Formula 107). The layers were separated and the organic was concentrated to dryness. The residue was chromatographed to afford an additional yield of the title compound. 1HNMR (300 MHz, DMSO-d6) δ (ppm)8.15(d,1H), 7.65(S,1H), 7.60(d,1H), 7.40–7.20(m,5H), 5.75(d,1H), 5.15(d,1H), 4.40(t,1H), 2.25(m,1H), 1.40–1.15(m,10H), 0.08(d, 3H), 0.35(d,3H).

Aufarbeitung

  1. customA dry 3-necked, round bottomed flask, equipped with a magnetic stirrer and nitrogen inlet
  2. customprepared
  3. customreaction
  4. filtrationThe formed white solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-733fc06713a8417e8f37c2a6cb84eaa7
Quelldatensatz
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07161002B2

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