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

HRID 388083

反応式

HRID 388083 の反応式
[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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

(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]+.

後処理

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

出典と根拠

ORDレコード
ord-fb8e230fb2984b3999726018cc9e59e0
出典データセット
uspto-grants-2013_02
特許番号
US08372976B2

関連ノート

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