Potassium Carbonate → N-(4-{4-(5-(2-Methoxyethoxy)pyrazin-2-ylthio)-2,6-dimethylphenyl}thiazol-2-yl)isonicotinamide

HRID 1465575Notes

Reaction equation

I[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[N:10]=[C:11]([NH:14][C:15](=[O:22])[C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[S:12][CH:13]=2)=[C:4]([CH3:23])[CH:3]=1.[CH3:24][O:25][CH2:26][CH2:27][O:28][C:29]1[N:30]=[CH:31][C:32]([SH:35])=[N:33][CH:34]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cu](I)I>[CH3:24][O:25][CH2:26][CH2:27][O:28][C:29]1[N:30]=[CH:31][C:32]([S:35][C:2]2[CH:7]=[C:6]([CH3:8])[C:5]([C:9]3[N:10]=[C:11]([NH:14][C:15](=[O:22])[C:16]4[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=4)[S:12][CH:13]=3)=[C:4]([CH3:23])[CH:3]=2)=[N:33][CH:34]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 25-1 (3.00 g, 6.89 mmol), 5-(2-methoxyethoxy)pyrazine-2-thiol (27-2, 2.57 g, 13.8 mmol), copper iodide (66.0 mg, 0.35 mmol), and potassium carbonate (2.86 g, 20.7 mmol) in 13.8 mL of DMF was stirred at 100° C. for 7.0 h. The reaction mixture was concentrated under reduced pressure and purified by column chromatography on silica gel (EtOAc:hexnaes=2:1 as eluant) to give N-(4-{4-(5-(2-methoxyethoxy)pyrazin-2-ylthio)-2,6-dimethylphenyl}thiazol-2-yl)isonicotinamide (27, 2.00 g) as light yellow solids in 59% yield: 1H NMR (500 MHz, CDCl3) δ 8.75 (d, J=4.0 Hz, 2 H), 8.19 (d, J=1.0 Hz, 1 H), 8.00 (d, J=1.0 Hz, 1H), 7.63 (d, J=5.0 Hz, 2 H), 6.96 (s, 1 H), 6.79 (s, 2 H), 4.44 (t, J=4.5 Hz, 2 H), 3.72 (t, J=4.5 Hz, 2 H), 3.41 (s, 3 H), 1.95 (s, 6 H). ESI-MS: m/z 494.2 (M+H)+.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
custompurified by column chromatography on silica gel (EtOAc:hexnaes=2:1 as eluant)

Sources & evidence

ORD record: ord-102d0ade75c141f98e69e97a06110987
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999983B2

Reaction notes

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