Potassium Carbonate → 1-(4-Methoxybenzyl)-6-(quinolin-5-YL)-1H-imidazo[4,5-B]pyrazin-2(3H)-one

HRID 388083

반응식

HRID 388083 반응식
[NH2:1][C:2]1[C:3]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[N:4][C:5]([C:8]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[N:13]3)=[CH:6][N:7]=1.BrC1N=C(NCC2C=C[C:40]([O:43]C)=CC=2)C(N)=NC=1.N1C2C=CC=C(B(O)O)C=2C=CC=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C)C=O.O>[CH3:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][N:18]2[C:3]3=[N:4][C:5]([C:8]4[CH:17]=[CH:16][CH:15]=[C:14]5[C:9]=4[CH:10]=[CH:11][CH:12]=[N:13]5)=[CH:6][N:7]=[C:2]3[NH:1][C:40]2=[O:43])=[CH:21][CH:22]=1

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 5153389Quinolin-5-ylboronic acidHCID 248204296-Bromo-N2-(4-methoxybenzyl)pyrazine-2,3-diamineHCID 66699817(3-Amino-6-(5-quinolyl)pyrazin-2-yl)[(4-methoxyphenyl)methyl]amine

생성물 1

HCID 666996241-(4-Methoxybenzyl)-6-(quinolin-5-YL)-1H-imidazo[4,5-B]pyrazin-2(3H)-one수율 15%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

(3-Amino-6-(5-quinolyl)pyrazin-2-yl)[(4-methoxyphenyl)methyl]amine. 6-Bromo-N2-(4-methoxybenzyl)pyrazine-2,3-diamine (0.928 g, 3.00 mmol), quinoline-5-boronic acid (0.675 g, 3.9 mmol), tetrakis(triphenylphosphine)palladium (0.306 g, 0.265 mmol), potassium carbonate (1.10 g, 7.95 mmol), water (7 ml) and dimethylformamide (35 mL) were reacted according to General Procedure B. The crude material was purified via Biotage silica gel chromatography (0-10% methanol in dichloromethane) followed by triturating with water/methanol to afford the title compound (0.165 g, 15% yield). MS (ESI) m/z 358.3 [M+1]+.

후처리

  1. customThe crude material was purified via Biotage silica gel chromatography (0-10% methanol in dichloromethane)
  2. customby triturating with water/methanol

출처 및 근거

ORD 기록
ord-fb8e230fb2984b3999726018cc9e59e0
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372976B2

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