4-Bromobenzyl isocyanate → N-(4-bromobenzyl)-N'-(1,3-dimethyl-5-isoquinolinyl)urea

HRID 2056886ノート

反応式

HRID 2056886 の反応式
[CH3:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([NH2:12])[C:6]=2[CH:5]=[C:4]([CH3:13])[N:3]=1.[Br:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][N:22]=[C:23]=[O:24])=[CH:17][CH:16]=1>C1(C)C=CC=CC=1>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][NH:22][C:23]([NH:12][C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:6]=2[CH:5]=[C:4]([CH3:13])[N:3]=[C:2]3[CH3:1])=[O:24])=[CH:19][CH:20]=1

参加物

4

反応物 2

HCID 43746174-Bromobenzyl isocyanateHCID 223376241,3-Dimethylisoquinolin-5-amine

生成物 1

HCID 11740716N-(4-bromobenzyl)-N'-(1,3-dimethyl-5-isoquinolinyl)urea

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
87.5 °C

実験手順

The product from Example 178A(375 mg, 2.2 mmol) in toluene (7 mL) was treated with 1-bromo-4-(isocyanatomethyl)benzene (0.31 mL, 2.2 mmol). After stirring at 85-90° C. for 3 hours, the mixture was cooled to room temperature and filtered. The filter cake was treated with methanolic HCl to provide the title compound as the hydrochloride salt. 1H NMR (300 MHz, DMSO-d6) δ 8.62 (s, 1H), 8.17 (d, 1H, J=7.8 Hz), 7.80 (d, 1H, J=8.5 Hz), 7.45-7.60 (m, 4H), 7.32 (d, 2H, J=8.1 Hz), 7.06 (t, 1H, 5.7 Hz), 4.34 (d, 2H, 5.8 Hz), 2.84 (s, 3H), 2.75 (s, 3H); MS (ESI+) m/z 383/385 (M+H, 79Br/81Br).

後処理

  1. temperaturethe mixture was cooled to room temperature
  2. filtrationfiltered
  3. additionThe filter cake was treated with methanolic HCl

出典と根拠

ORDレコード
ord-a74fa34e5dc84ab780a9201881262148
出典データセット
uspto-grants-2008_02
特許番号
US07335678B2

反応ノート

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