3-Methylbenzoic acid → HCID 24963673, Verbindung

HRID 1868276Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1868276
[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([OH:9])=O)[CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[NH2:24][CH2:25][C:26]1[CH:35]=[CH:34][CH:33]=[C:32]2[C:27]=1[C:28](=[O:45])[N:29]([CH:37]1[CH2:42][CH2:41][C:40](=[O:43])[NH:39][C:38]1=[O:44])[C:30]([CH3:36])=[N:31]2>CN(C=O)C>[O:44]=[C:38]1[CH:37]([N:29]2[C:28](=[O:45])[C:27]3[C:32](=[CH:33][CH:34]=[CH:35][C:26]=3[CH2:25][NH:24][C:7](=[O:9])[C:3]3[CH:4]=[CH:5][CH:6]=[C:1]([CH3:10])[CH:2]=3)[N:31]=[C:30]2[CH3:36])[CH2:42][CH2:41][C:40](=[O:43])[NH:39]1

Komponenten

5

Edukt 3

HCID 74183-Methylbenzoic acidHCID 682631,1'-CarbonyldiimidazoleHCID 249683051015474-47-1

Produkt 1

HCID 24963673HCID 24963673, VerbindungAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of m-toluic acid (0.24 g, 1.8 mmol) in DMF (8 mL) in a 40° C. oil bath, was added 1.1′ carbonyldiimidazole (0.31 g, 1.9 mmol) and stirred for one hour. To the mixture, 3-(5-aminomethyl-2-methyl-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione hydrogen chloride (0.59 g, 1.8 mmol) was added, and the mixture was stirred for 45 minutes. The solvent was evaporated, and the residue was purified by flash column chromatography (Silica gel, methanol/methylene chloride 4%/96%) to give N-[3-(2,6-dioxo-piperidin-3-yl)-2-methyl-4-oxo-3,4-dihydro-quinazolin-5-ylmethyl]-3-methyl-benzamide as a light green solid (560 mg, 76% yield); HPLC, Waters Symmetry C18, 5 μm, 3.9×150 mm, 1 mL/min, 240 nm, 10/90 CH3CN/0.1% H3PO4, grad. to 95/5 in 5 min, kept 5 min, 6.00 min (99.2%); mp, 263-265° C.; 1HNMR (DMSO-d6) 2.18-2.21 (m, 1H, CHH), 2.38 (s, 3H, CH3Ar), 2.59-2.88 (m, 6H, CHCH2, CH3), 4.95-5.12 (m, 2H, CH2NH), 5.26 (dd, J=6, 11 Hz, 1H, CH), 7.33-7.76 (m, 7H, Ar), 8.89 (t, J=5 Hz, 1H, CH2NH), 11.05 (s, 1H, NH); 13C NMR (DMSO-d6) δ 20.83, 20.92, 23.29, 30.60, 42.12, 56.52, 117.65, 123.98, 124.32, 125.40, 127.76, 128.26, 131.85, 133.93, 134.23, 137.65, 141.04, 148.50, 154.80, 161.11, 166.39, 169.53, 172.61. LCMS MH=419; Anal Calcd For C23H22N4O4+0.6H2O: C, 64.36; H, 5.45; N, 13.05. Found: C, 64.36; H, 5.24; N, 13.22.

Aufarbeitung

  1. stirringthe mixture was stirred for 45 minutes
  2. customThe solvent was evaporated
  3. customthe residue was purified by flash column chromatography (Silica gel, methanol/methylene chloride 4%/96%)

Quellen und Nachweise

ORD-Eintrag
ord-2bee1e246b3f43628056842e170cdced
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07635700B2

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