Mechlorethamine → 7-Methyl-5-(4-methyl-piperazin-1-ylmethyl)-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one

HRID 2427720

반응식

HRID 2427720 반응식
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[C:8](=[O:13])[N:7]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=1)[CH2:6]2.Cl[CH2:27][CH2:28][N:29]([CH2:31][CH2:32]Cl)[CH3:30].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:12][C:10]1[CH:11]=[C:3]([CH2:2][N:1]2[CH2:32][CH2:31][N:29]([CH3:30])[CH2:28][CH2:27]2)[CH:4]=[C:5]2[C:9]=1[C:8](=[O:13])[N:7]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:23])[F:24])=[CH:17][CH:16]=1)[CH2:6]2

참가 물질

5

반응물 3

HCID 4033MechlorethamineHCID 11430Potassium CarbonateHCID 579493205-Aminomethyl-7-methyl-2-(4-trifluoromethoxybenzyl)-2,3-dihydroisoindol-1-one

생성물 1

HCID 579494067-Methyl-5-(4-methyl-piperazin-1-ylmethyl)-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one수율 31%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
110 °C

실험 절차

In sealed vial, a mixture of 5-aminomethyl-7-methyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.104 g, 0.3 mmol), bis(2-chloro-ethyl)-methyl-amine (0.077 g, 0.4 mmol), and K2CO3 (0.083 g, 0.6 mmol) in DMF (3 mL) was stirred at 110° C. for 16 h. After this time, the GC-MS of the reaction mixture indicated the completion of reaction. The reaction was cooled to ambient temperature and the solids removed by filtration. The filtrate was concentrated. Silica gel column chromatography of the resulting material using 5:1 CHCl3-MeOH afforded 7-methyl-5-(4-methyl-piperazin-1-ylmethyl)-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.040 g, 31%). 1H NMR (300 MHz, CDCl3): δ (ppm) 2.24 (s, 3H), 2.34-2.52 (m, 8H), 2.74 (s, 3H), 3.49 (s, 2H), 4.20 (s, 2H), 4.76 (s, 2H), 7.15-7.37 (m, 6H). GC-MS: m/z 433 (M)+.

후처리

  1. customthe completion of reaction
  2. temperatureThe reaction was cooled to ambient temperature
  3. customthe solids removed by filtration
  4. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-d6fdfeea6ef14a189a92dc3c871e7335
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07968570B2

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