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

HRID 887275노트

반응식

HRID 887275 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ffe2294bacdc43d8b22371a4e60730da
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247413B2

반응 노트

불러오는 중…