Potassium Iodide → 3-[7-{2-[isopropyl(methyl)amino]ethoxy}-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoic acid

HRID 506990ノート

反応式

HRID 506990 の反応式
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][N:11]([C:16]3[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=3[CH3:25])[C:19]([OH:21])=[O:20])[C:12]2=[O:15])=[CH:7][CH:6]=1.C[CH2:27][N:28](C(C)C)[CH:29]([CH3:31])[CH3:30].[I-].[K+].CNC(C)C.[N-]=C=O>CC(N(C)C)=O.C(Cl)Cl>[CH:29]([N:28]([CH3:27])[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][N:11]([C:16]3[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=3[CH3:25])[C:19]([OH:21])=[O:20])[C:12]2=[O:15])=[CH:7][CH:6]=1)([CH3:31])[CH3:30]

参加物

8

反応物 5

HCID 4875Potassium IodideHCID 78485N-MethylisopropylamineHCID 81531DiisopropylethylamineHCID 105034IsocyanateHCID 670185953-[7-(2-chloroethoxy)-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoic acid

生成物 1

HCID 670185933-[7-{2-[isopropyl(methyl)amino]ethoxy}-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoic acid

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 31374Dimethylacetamide溶媒

実験手順

3-[7-(2-chloroethoxy)-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoic acid (504 mg), DIPEA (0.7 ml), potassium iodide (332 mg) and N-methylisopropylamine (0.42 ml) in DMA (4 ml) was heated under microwave irradiation conditions (Personal Chemistry Emrys Optimizer with 300 W magnetron) at 120° C. for 30 minutes. The mixture was diluted with methylene chloride (25 ml), isocyanate resin (CombiZorb) (7.67 g) was added and stirred at room temperature for 18 hours. The resin was removed by filtration and the filtrate was washed with water. The aqueous phase 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 3-[7-{2-[isopropyl(methyl)amino]ethoxy}-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoic acid as a pale brown solid (110 mg); NMR Spectrum: (DMSOd6) 1.00 (m, 6H), 2.15 (s, 3H), 2.30 (s, 3H), 2.45 (s, 1H), 2.85 (m, 2H), 4.15 (m, 2H), 6.70 (m, 1H), 7.20 (m, 1H), 7.40 (m, 1H), 7.55 (m, 1H), 7.70 (m, 2H), 7.80 (m, 1H), 7.95 (m, 1H); Mass Spectrum: M+H+ 395.

後処理

  1. additionwas added
  2. customThe resin was removed by filtration
  3. washthe filtrate was washed with water
  4. customThe aqueous phase was purified by column chromatography on an ion exchange column (isolute SCX column from International Sorbent Technology Limited, Henoed, Mid-Glamorgan, UK)
  5. additiona 99:1 mixture of methanol and aqueous ammonia solution

出典と根拠

ORDレコード
ord-7097e5ada7994541b30f95132dd944a1
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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