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

HRID 1432927ノート

反応式

HRID 1432927 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-7c87a04d46d2483886772d51328d22a5
出典データセット
uspto-grants-2009_11
特許番号
US07612075B2

反応ノート

読み込み中…