1,2-Dichloro-4-(isocyanatomethyl)benzene → N-(3,4-dichlorobenzyl)-N'-(3-methyl-5-isoquinolinyl)urea

HRID 887275

反応式

HRID 887275 の反応式
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH3:12])[N:6]=[CH:7]2.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]=[C:22]=[O:23])=[CH:16][C:15]=1[Cl:24]>C1(C)C=CC=CC=1>[Cl:24][C:15]1[CH:16]=[C:17]([CH:18]=[CH:19][C:14]=1[Cl:13])[CH2:20][NH:21][C:22]([NH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH3:12])[N:6]=[CH:7]2)=[O:23]

参加物

4

反応物 2

HCID 27333681,2-Dichloro-4-(isocyanatomethyl)benzeneHCID 122120553-Methylisoquinolin-5-amine

生成物 1

HCID 9998596N-(3,4-dichlorobenzyl)-N'-(3-methyl-5-isoquinolinyl)urea

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

5-Amino-3-methylisoquinoline (390 mg, 2.47 mmol) and the product from Example 194A (0.36 mL, 2.45 mmol) were heated in toluene (10 mL) at 80° for 2.5 hours. Upon cooling to room temperature, a precipitate formed, which was collected by filtration, washed with toluene, and air-dried. Remaining impurities were removed by slurrying the solid in 9:1 CH2Cl2:CH3OH and then filtering the mixture to provide the title compound. The corresponding hydrochloride salt was formed by treatment of the free base with methanolic HCl. 1H NMR (300 MHz, DMSO-d6) δ 9.17 (s, 1H), 8.27 (s, 1H), 8.17 (dd, 1H, J=7.8 Hz, 1.0 Hz), 7.74 (s, 1H), 7.71 (d, 1H, J=8.1 Hz), 7.61 (m, 2H), 7.50 (t, 1H, J=8.0 Hz), 7.35 (dd, 1H, J=8.3 Hz, 2.2 Hz), 7.12 (t, 1H, 5.9 Hz), 4.37 (d, 2H, J=6.1 Hz), 2.65 (s, 3H); MS (ESI+) m/z 360/362 (M+H, 35Cl/37Cl).

後処理

  1. customa precipitate formed
  2. filtrationwhich was collected by filtration
  3. washwashed with toluene
  4. customair-dried
  5. customRemaining impurities were removed
  6. filtrationCH3OH and then filtering the mixture

出典と根拠

ORDレコード
ord-ffe2294bacdc43d8b22371a4e60730da
出典データセット
uspto-grants-2012_08
特許番号
US08247413B2

関連ノート

読み込み中…