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

HRID 1432927노트

반응식

HRID 1432927 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-7c87a04d46d2483886772d51328d22a5
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612075B2

반응 노트

불러오는 중…