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

HRID 1014693ノート

反応式

HRID 1014693 の反応式
[CH3:1][C:2]1[N:3]=[C:4]([NH2:27])[C:5]([NH:18][C@@H:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH3:20])=[N:6][C:7]=1[C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2.BrC1N=C(N[C@@H](C2C=CC=CC=2)C)C(N)=NC=1C.N1C2C=CC=C(B(O)O)C=2C=CC=1.[C:59](=O)([O-])[O-:60].[K+].[K+]>O.CN(C)C=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][C:2]1[N:3]=[C:4]2[NH:27][C:59](=[O:60])[N:18]([C@@H:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH3:20])[C:5]2=[N:6][C:7]=1[C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 5153389Quinolin-5-ylboronic acidHCID 688535175-Methyl-N2-((R)-1-phenylethyl)-6-(quinolin-5-yl)pyrazine-2,3-diamineHCID 86626390(R)-6-Bromo-5-methyl-N2-(1-phenylethyl)pyrazine-2,3-diamine

生成物 1

HCID 666995935-Methyl-1-((R)-1-phenylethyl)-6-(quinolin-5-YL)-1H-imidazo[4,5-B]pyrazin-2(3H)-one収率 67%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

5-Methyl-N2—((R)-1-phenylethyl)-6-(quinolin-5-yl)pyrazine-2,3-diamine. (R)-6-Bromo-5-methyl-N2-(1-phenylethyl)pyrazine-2,3-diamine (0.534 g, 1.74 mmol), quinoline-5-boronic acid (0.331 g, 1.91 mmol), tetrakis(triphenylphosphine) palladium (0.20 g, 0.175 mmol), and potassium carbonate (0.96 g, 6.96 mmol) in water (4 mL) and dimethylformamide (15 mL) was reacted according to General Procedure B and purified via Biotage silica gel chromatography (0-10% methanol in dichloromethane, 40M column) and the resultant solid triturated with water/methanol to afford the title compound (0.42 g, 67% yield). MS (ESI) m/z 356.4 [M+1]+.

後処理

  1. custompurified via Biotage silica gel chromatography (0-10% methanol in dichloromethane, 40M column)
  2. customthe resultant solid triturated with water/methanol

出典と根拠

ORDレコード
ord-c72963b65ceb47bbbcc449e89b547450
出典データセット
uspto-grants-2011_07
特許番号
US07981893B2

反応ノート

読み込み中…