Potassium Carbonate → 3-(5-(3-(ethylsulfonyl)phenyl)-3-methyl-9H-pyrido[2,3-b]indol-8-yloxy)-N,N-dimethylpropan-1-amine

HRID 1642564

反応式

[CH2:1]([S:3]([C:6]1[CH:7]=[C:8]([C:12]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]3[C:13]=2[C:14]2[CH:25]=[C:24]([CH3:26])[CH:23]=[N:22][C:15]=2[NH:16]3)[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4])[CH3:2].[CH3:27][N:28]([CH3:43])[CH2:29][CH2:30][CH2:31]OS(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([S:3]([C:6]1[CH:7]=[C:8]([C:12]2[CH:20]=[CH:19][C:18]([O:21][CH2:31][CH2:30][CH2:29][N:28]([CH3:43])[CH3:27])=[C:17]3[C:13]=2[C:14]2[CH:25]=[C:24]([CH3:26])[CH:23]=[N:22][C:15]=2[NH:16]3)[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4])[CH3:2]

参加物

反応条件

温度: 200 °C

実験手順

A 5 mL microwave vial was charged with Compound 157 (290 mg, 0.79 mmol), 3-(dimethylamino)propyl-4-methylbenzenesulfonate (224 mg, 0.87 mmol), potassium carbonate (218 mg, 1.58 mmol) and 2 mL of anhydrous DMF, under nitrogen atmosphere. The reaction mixture was heated at 200° C. for 30 min. in microwave with high absorption. The reaction was quenched with addition of water, and the solid precipitate out was collected by filtration and purified through preparative HPLC to provide title compound (1438 mg, 40%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.17 (t, J=7.33 Hz, 3 H) 1.99 (qd, J=6.61, 6.44 Hz, 2 H) 2.20 (s, 6 H) 2.26 (s, 3 H) 2.53-2.56 (m, 2 H) 3.41 (q, J=7.33 Hz, 2 H) 4.25 (t, J=6.19 Hz, 2 H) 7.05-7.09 (m, 1 H) 7.11-7.14 (m, 1 H) 7.54 (d, J=1.52 Hz, 1 H) 7.85 (t, J=7.83 Hz, 1 H) 7.98 (t, J=6.95 Hz, 2 H) 8.06-8.08 (m, 1 H) 8.27 (d, J=1.77 Hz, 1 H) 12.13 (s, 1 H); [M+H] calc'd for C25H30N3O3S, 452.2; found, 452.4.

後処理

customThe reaction was quenched with addition of water
filtrationthe solid precipitate out was collected by filtration
custompurified through preparative HPLC

出典と根拠

ORDレコード: ord-878974a300dd43f9bdeaaaf55efab833
出典データセット: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08119655B2

反応式

参加物

反応物 3

生成物 1

試薬・触媒・溶媒 1

反応条件

実験手順

後処理

出典と根拠

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