Methanol → methyl 3-[7-[3-(dimethylamino)propyl]-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoate

HRID 506999노트

반응식

HRID 506999 반응식
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][C:16]([C:22]#[C:23][CH2:24][N:25]3[CH2:30]COC[CH2:26]3)=[CH:17][CH:18]=2)[C:13]1=[O:31].CO.C(OCC)(=O)C>C(O)C.[Pd]>[CH3:30][N:25]([CH3:26])[CH2:24][CH2:23][CH2:22][C:16]1[CH:15]=[C:14]2[C:19]([CH:20]=[CH:21][N:12]([C:3]3[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=3[CH3:1])[C:6]([O:8][CH3:9])=[O:7])[C:13]2=[O:31])=[CH:18][CH:17]=1

참가 물질

6

반응물 3

HCID 887MethanolHCID 8857Ethyl AcetateHCID 67018671Methyl 4-methyl-3-[7-(3-morpholin-4-ylprop-1-yn-1-yl)-1-oxoisoquinolin-2(1H)-yl]benzoate

생성물 1

HCID 67018581methyl 3-[7-[3-(dimethylamino)propyl]-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoate수율 91.2%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

Methyl 4-methyl-3-[7-(3-morpholin-4-ylprop-1-yn-1-yl)-1-oxoisoquinolin-2(1H)-yl]benzoate (292 mg) and 10% Pd/C (30 mg) were stirred in a mixture of ethanol (2 ml)/methanol (4 ml)/ethyl acetate (2 ml) under an atmosphere of hydrogen at room temperature for 17 hours. The catalyst was removed by filtration through a microfibre filter and the filtrate was concentrated to yield an oil. The oil was purified by column chromatography on an ion exchange column (isolute SCX column from International Sorbent Technology Limited, Henoed, Mid-Glamorgan, UK) using initially methanol and then a 99:1 mixture of methanol and aqueous ammonia solution to yield methyl 3-[7-[3-(dimethylamino)propyl]-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoate as a brown oil (242 mg); NMR Spectrum: (DMSOd6) 1.79 (m, 2H), 2.14 (s, 3H), 2.28-2.36 (m, 6H), 2.77 (t, 2H), 3.57 (m, 4H), 3.86 (s, 3H), 6.72 (d, 1H), 7.30 (d, 1H), 7.59 (d, 1H), 7.67 (m, 2H), 7.83 (s, 1H), 7.98 (d, 1H), 8.08 (s, 1H); Mass Spectrum: M+H+ 421.

후처리

  1. customThe catalyst was removed by filtration through
  2. filtrationa microfibre filter
  3. concentrationthe filtrate was concentrated
  4. customto yield an oil
  5. customThe oil was purified by column chromatography on an ion exchange column (isolute SCX column from International Sorbent Technology Limited, Henoed, Mid-Glamorgan, UK)
  6. additiona 99:1 mixture of methanol and aqueous ammonia solution

출처 및 근거

ORD 기록
ord-c52e7811d19a4c219ab9e79d0ef71a97
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786115B2

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