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

HRID 388099노트

반응식

HRID 388099 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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]+.

후처리

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

출처 및 근거

ORD 기록
ord-3b72cdb49a98408e944f5c4d37ed84e2
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372976B2

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