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

HRID 506999ノート

反応式

HRID 506999 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c52e7811d19a4c219ab9e79d0ef71a97
出典データセット
uspto-grants-2010_08
特許番号
US07786115B2

反応ノート

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