Homophthalic anhydride → 3-(1,3-dioxo-3,4-dihydroisoquinolin-2(1H)-yl)-N-cyclopropyl-4-methylbenzamide

HRID 506970

반응식

HRID 506970 반응식
[C:1]1(=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C:3](=[O:11])O1.[NH2:13][C:14]1[CH:15]=[C:16]([CH:23]=[CH:24][C:25]=1[CH3:26])[C:17]([NH:19][CH:20]1[CH2:22][CH2:21]1)=[O:18]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[O:12]=[C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C:3](=[O:11])[N:13]1[C:14]1[CH:15]=[C:16]([CH:23]=[CH:24][C:25]=1[CH3:26])[C:17]([NH:19][CH:20]1[CH2:21][CH2:22]1)=[O:18]

참가 물질

5

반응물 2

HCID 12801Homophthalic anhydrideHCID 119838543-amino-N-cyclopropyl-4-methylbenzamide

생성물 1

HCID 670185863-(1,3-dioxo-3,4-dihydroisoquinolin-2(1H)-yl)-N-cyclopropyl-4-methylbenzamide수율 56.3%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
150 °C

실험 절차

A suspension of 1H-isochromene-1,3(4H)-dione (400 mg) and 3-amino-N-cyclopropyl-4-methylbenzamide (514 mg) in toluene (3 ml) was heated under microwave irradiation conditions (Personal Chemistry Emrys Optimizer with 300 W magnetron) at 150° C. for 60 minutes. The reaction mixture was diluted with ethyl acetate and washed with 2N HCl, water, brine, dried (magnesium sulfate) and concentrated to a foam which was purified by column chromatography with a gradient of iso-hexane to 70% ethyl acetate/iso-hexane to yield 3-(1,3-dioxo-3,4-dihydroisoquinolin-2(1H)-yl)-N-cyclopropyl-4-methylbenzamide as a solid (464 mg); NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.69 (m, 2H), 2.09 (s, 3H), 2.85 (m, 1H), 4.33 (d, 1H), 4.41 (d, 1H), 7.42 (d, 1H), 7.49-7.55 (m, 2H), 7.65 (s, 1H), 7.74 (t, 1H), 7.80 (d, 1H), 8.09 (d, 1H), 8.39 (d, 1H); Mass Spectrum: M+H+ 335.

후처리

  1. washwashed with 2N HCl, water, brine
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated to a foam which
  4. customwas purified by column chromatography with a gradient of iso-hexane to 70% ethyl acetate/iso-hexane

출처 및 근거

ORD 기록
ord-d886018a616847daabcc9736c50a7429
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786115B2

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