Hydrogen Bromide → 1-(4-Amino-quinazoline-7-ylmethyl)-3-methoxymethyl-piperazine-2-one

HRID 1432927Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1432927
C(OC([N:11]1[CH2:16][CH2:15][NH:14][C:13](=[O:17])[CH:12]1[CH2:18][O:19][CH3:20])=O)C1C=CC=CC=1.I[C:22]1[C:23]([NH2:28])=[N:24][CH:25]=[CH:26][CH:27]=1.Br>C(O)(=O)C>[NH2:28][C:23]1[C:22]2[C:23](=[CH:22][C:27]([CH2:26][N:14]3[CH2:15][CH2:16][NH:11][CH:12]([CH2:18][O:19][CH3:20])[C:13]3=[O:17])=[CH:26][CH:27]=2)[N:24]=[CH:25][N:24]=1

Komponenten

5

Edukt 3

HCID 260Hydrogen BromideHCID 27631512-Amino-3-iodopyridineHCID 544122632-Methoxymethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester

Produkt 1

HCID 179852231-(4-Amino-quinazoline-7-ylmethyl)-3-methoxymethyl-piperazine-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

To a solution of 2-methoxymethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester (5.8 g, 13.3 mmol) in 50 mL of acetic acid is added dropwise, 20 mL of a 30%HBr in AcOH solution. The solution is stirred for 1 hour. After this time, the solution is concentrated. The resulting crude product is purified by column chromatography eluting with CH2Cl2:MeOH:NH4OH (20:5:1). The title compound (2.0 g, 6.6 mmol) is obtained as a white solid. 1H NMR (d6-DMSO, 300 MHz) δ8.60 (s, 1H), 7.72 (m, 2H), 7.48 (d, 1H), 5.60 (bs, 2H), 4.72 (AB, 2H), 3.87 (m, 2H), 3.71 (m, 1H), 3.42 (m, 1H), 3.40 (s, 3H), 3.19 (m, 2H), 3.02 (m, 1H). MS (ion spray) m/z 302, (M+H).

Aufarbeitung

  1. concentrationAfter this time, the solution is concentrated
  2. customThe resulting crude product is purified by column chromatography
  3. washeluting with CH2Cl2:MeOH:NH4OH (20:5:1)

Quellen und Nachweise

ORD-Eintrag
ord-7c87a04d46d2483886772d51328d22a5
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612075B2

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