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

HRID 1014687Notes

Reaction equation

HRID 1014687 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 68853527(S)-N2-(1-phenylpropyl)-6-(quinolin-5-yl)pyrazine-2,3-diamineHCID 86626385(S)-6-Bromo-N2-(1-phenylpropyl)pyrazine-2,3-diamine

Product 1

HCID 66699761(S)-1-(1-Phenylpropyl)-6-(quinolin-5-YL)-1H-imidazo[4,5-B]pyrazin-2(3H)-oneYield 77%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(S)—N2-(1-phenylpropyl)-6-(quinolin-5-yl)pyrazine-2,3-diamine. (S)-6-Bromo-N2-(1-phenylpropyl)pyrazine-2,3-diamine (0.560 g, 1.83 mmol), quinoline-5-boronic acid (0.348 g, 2.01 mmol), tetrakis(triphenylphosphine)palladium (0.211 g, 0.183 mmol), potassium carbonate (1.01 g, 7.32 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 (0.500 g, 77% yield). MS (ESI) m/z 356.3 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-d02bf0c3e8b545878e9a5b2da2394ae1
Source dataset
uspto-grants-2011_07
Patent number
US07981893B2

Reaction notes

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