Potassium Carbonate → (R)-1-(1-PHENYLPROPYL)-6-(QUINOLIN-5-YL)-1H-IMIDAZO[4,5-b]PYRAZIN-2(3H)-ONE

HRID 388093

Reaction equation

HRID 388093 reaction equation
[C:1]1([C@H:7]([NH:10][C:11]2[C:16]([NH2:17])=[N:15][CH:14]=[C:13]([C:18]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:19]=3[CH:20]=[CH:21][CH:22]=[N:23]4)[N:12]=2)[CH2:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.BrC1N=C(N[C@@H](C2C=CC=CC=2)CC)C(N)=NC=1.N1C2C=CC=C(B(O)O)C=2C=CC=1.[C:59](=O)([O-])[O-:60].[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>[C:1]1([C@H:7]([N:10]2[C:11]3=[N:12][C:13]([C:18]4[CH:27]=[CH:26][CH:25]=[C:24]5[C:19]=4[CH:20]=[CH:21][CH:22]=[N:23]5)=[CH:14][N:15]=[C:16]3[NH:17][C:59]2=[O:60])[CH2:8][CH3:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 5153389Quinolin-5-ylboronic acidHCID 68853964(R)-N2-(1-phenylpropyl)-6-(quinolin-5-yl)pyrazine-2,3-diamineHCID 86626386(R)-6-Bromo-N2-(1-phenylpropyl)pyrazine-2,3-diamine

Product 1

HCID 66699594(R)-1-(1-PHENYLPROPYL)-6-(QUINOLIN-5-YL)-1H-IMIDAZO[4,5-b]PYRAZIN-2(3H)-ONEYield 93%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(R)-N2-(1-phenylpropyl)-6-(quinolin-5-yl)pyrazine-2,3-diamine. (R)-6-Bromo-N2-(1-phenylpropyl)pyrazine-2,3-diamine (0.440 g, 1.43 mmol), quinoline-5-boronic acid (0.273 g, 1.58 mmol), tetrakis(triphenylphosphine)palladium (0.165 g, 0.143 mmol), potassium carbonate (0.789 g, 5.72 mmol), water (8 mL) and dimethylformamide (30 mL) were reacted according to General Procedure B. The crude was purified via Biotage silica gel chromatography (0-10% methanol/dichloromethane, 40S column) to afford the title compound (0.476 g, 93% yield). MS (ESI) m/z 356.4 [M+1]+.

Workup

  1. customThe crude was purified via Biotage silica gel chromatography (0-10% methanol/dichloromethane, 40S column)

Sources & evidence

ORD record
ord-8a0acac74f0f457897a5d23e595e3049
Source dataset
uspto-grants-2013_02
Patent number
US08372976B2

Linked notes

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