1-Propanol → N-cyclopropyl-4-[8-(isobutylamino)-6-(4-vinylphenyl)imidazo[1,2-a]pyrazin-3-yl]benzamide

HRID 925595ノート

反応式

HRID 925595 の反応式
Br[C:2]1[N:3]=[C:4]([NH:23][CH2:24][CH:25]([CH3:27])[CH3:26])[C:5]2[N:6]([C:8]([C:11]3[CH:22]=[CH:21][C:14]([C:15]([NH:17][CH:18]4[CH2:20][CH2:19]4)=[O:16])=[CH:13][CH:12]=3)=[CH:9][N:10]=2)[CH:7]=1.[CH:28]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)=[CH2:29].C(O)CC.C(=O)([O-])[O-].[K+].[K+]>C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH:18]1([NH:17][C:15](=[O:16])[C:14]2[CH:21]=[CH:22][C:11]([C:8]3[N:6]4[CH:7]=[C:2]([C:33]5[CH:34]=[CH:35][C:30]([CH:28]=[CH2:29])=[CH:31][CH:32]=5)[N:3]=[C:4]([NH:23][CH2:24][CH:25]([CH3:27])[CH3:26])[C:5]4=[N:10][CH:9]=3)=[CH:12][CH:13]=2)[CH2:20][CH2:19]1

参加物

8

反応物 4

HCID 10311-PropanolHCID 11430Potassium CarbonateHCID 27343934-Vinylphenylboronic acidHCID 509145924-(6-Bromo-8-(isobutylamino)imidazo[1,2-a]pyrazin-3-yl)-N-cyclopropylbenzamide

生成物 1

HCID 57407262N-cyclopropyl-4-[8-(isobutylamino)-6-(4-vinylphenyl)imidazo[1,2-a]pyrazin-3-yl]benzamide収率 97%

試薬・触媒・溶媒 3

HCID 11776Triphenylphosphine触媒HCID 178419050HCID 178419050、化合物触媒HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

A mixture of 0.5 g (1.17 mmol) 4-{6-bromo-8-[(2-methylpropyl)amino]imidazo[1,2-a]pyrazin-3-yl}-N-cyclopropylbenzamide (intermediate example 6-1), 345 mg (4-ethenylphenyl)boronic acid, 17 mL n-propanol, 1.75 mL of an aqueous 2M potassium carbonate solution, 15 mg triphenylphosphine, and 82 mg bis(triphenylphosphine)palladium was stirred at 120° C. for 2 hours. The solution was cooled, water added and extracted with dichloromethane. The organic phase was dried over sodium sulfate. After filtration and removal of solvent the residue was subjected to a column chromatography on silica gel to give 509 mg (97%) of the title compound. 1H-NMR (CDCl3): δ=0.67 (2H), 0.92 (2H), 1.06 (3H), 1.08 (3H), 2.09 (1H), 2.95 (1H), 3.58 (2H), 5.28 (1H), 5.80 (1H), 6.13 (1H), 6.34 (1H), 6.75 (1H), 7.47 (2H), 7.59 (1H), 7.65 (2H), 7.87 (2H), 7.92 (2H), 7.95 (1H) ppm.

後処理

  1. temperatureThe solution was cooled
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationAfter filtration and removal of solvent the residue

出典と根拠

ORDレコード
ord-8f9d0eb895514e74a655e8ead0598313
出典データセット
uspto-grants-2016_03
特許番号
US09284317B2

反応ノート

読み込み中…