4-Bromobenzyl isocyanate → N-[(4-bromophenyl)methyl]-N'-(1-methylisoquinolin-5-yl)urea

HRID 1791291

반응식

HRID 1791291 반응식
[CH3:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([NH2:12])[C:6]=2[CH:5]=[CH:4][N:3]=1.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]=[C:22]=[O:23])=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:20][NH:21][C:22]([NH:12][C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:6]=2[CH:5]=[CH:4][N:3]=[C:2]3[CH3:1])=[O:23])=[CH:18][CH:19]=1

참가 물질

4

반응물 2

HCID 43746174-Bromobenzyl isocyanateHCID 99894901-Methylisoquinolin-5-amine

생성물 1

HCID 10474287N-[(4-bromophenyl)methyl]-N'-(1-methylisoquinolin-5-yl)urea

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
90 °C

실험 절차

The product from Example 65A (480 mg, 3.04 mmol) in toluene (9 mL) was treated with 1-bromo-4-(isocyanatomethyl)benzene (0.43, 3.07 mmol) with stirring. After heating the mixture at 90° C. for 1 hour, the mixture was allowed to cool to room temperature, filtered, and the filter cake washed with toluene to provide the title compound. The corresponding di-hydrochloride salt was prepared using methanolic HCl (680 mg, 50%). 1H NMR (300 MHz, DMSO-d6) δ 8.74 (s, 1H), 8.38 (d, J=6.1 Hz, 1H), 8.25 (d, J=7.8 Hz, 1H), 7.78-7.85 (m, 2H), 7.53-7.61 (m, 3H), 7.32 (d, J=8.5 Hz, 2H), 7.11 (t, J=6.1 Hz, 1H), 4.34 (d, J=6.1 Hz, 2H), 2.88 (s, 3H); MS (ESI+) m/z 370/372 (M+H+, 79Br/81Br).

후처리

  1. temperatureto cool to room temperature
  2. filtrationfiltered
  3. washthe filter cake washed with toluene

출처 및 근거

ORD 기록
ord-53af5ae1b742411193551ab8a30ba92a
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074805B2

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