Water → HCID 25235778, Verbindung

HRID 453000Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 453000
[NH2:1][C:2]1[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:30])[CH2:21][O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:15][C:3]=1[C:4]([NH:6][CH:7]1[CH2:12][CH2:11][C:10](=[O:13])[NH:9][C:8]1=[O:14])=[O:5].C(OC)(OC)OC.[C:38]1(C)C=CC(S(O)(=O)=O)=C[CH:39]=1.O>CCOCC>[CH2:23]([O:22][CH2:21][C:20]([NH:19][C:16]1[CH:15]=[C:3]2[C:2](=[CH:18][CH:17]=1)[N:1]=[C:38]([CH3:39])[N:6]([CH:7]1[CH2:12][CH2:11][C:10](=[O:13])[NH:9][C:8]1=[O:14])[C:4]2=[O:5])=[O:30])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 68728792HCID 68728792, Verbindung

Produkt 1

HCID 25235778HCID 25235778, VerbindungAusbeute 118,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of 2-amino-5-(2-benzyloxy-acetylamino)-N-(2,6-dioxo-piperidin-3-yl)-benzamide (0.26 g, 0.6 mmol) and trimethyl orthoformate (2 mL) and p-toluene sulfonic acid (60 mg) in acetonotrile (10 mL) was heated to reflux for 21 hours. To the mixture, was added water (25 mL) and ether (25 mL). The suspension was filtered and washed with water (50 mL) and ethyl acetate (50 mL) to give 2-benzyloxy-N-[3-(2,6-dioxo-piperidin-3-yl)-2-methyl-4-oxo-3,4-dihydro-quinazolin-6-yl]-acetamide as a white solid (180 mg, 72% yield): HPLC: Waters Symmetry C18, 5 μm, 3.9×150 mm, 1 mL/min, 240 nm, 40/60 CH3CN/0.1% H3PO4, 2.87 min (99.3%); mp: 248-250° C.; 1H NMR (DMSO-d6) δ 2.14-2.16 (m, 1H, CHH), 2.62-2.87 (m, 3H, CH2, CHH), 4.15 (s, 2H, CH2), 4.64 (s, 2H, CH2), 5.49-5.50 (m, 1H, NCH), 7.31-7.41 (m, 5H, Ar), 7.68 (d, J=9 Hz, 1H, Ar), 8.06-8.10 (m, 1H, NH), 8.28 (s, 1H, CH), 8.55 (br, 1H, Ar), 10.24 (s, 1H, NH), 11.16 (s, 1H, NH; 13C NMR (DMSO-d6) δ 23.05, 31.48, 58 (br), 69.87, 72.92, 115.69, 122.15, 127.30, 128.16, 128.28, 128.34, 128.77, 137.98, 138.14, 144.06, 146.48, 160.10, 168.93, 170.43, 172.90; LCMS: MH=421; Anal Calcd for C22H20N4O5: C, 62.85; H, 4.79; N, 13.33. Found: C, 60.60; H, 4.29; N, 12.54.

Aufarbeitung

  1. temperatureto reflux for 21 hours
  2. filtrationThe suspension was filtered
  3. washwashed with water (50 mL) and ethyl acetate (50 mL)

Quellen und Nachweise

ORD-Eintrag
ord-dc54215bdb914449bbe7c523c88a9697
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492395B2

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