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

HRID 925595노트

반응식

HRID 925595 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 11776Triphenylphosphine촉매HCID 178419050HCID 178419050, 화합물촉매HCID 962Water용매

반응 조건

온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8f9d0eb895514e74a655e8ead0598313
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284317B2

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