Imidazole → [5-(2-Imidazol-1-yl-pyridin-4-yl)-4-methyl-thiazol-2-yl]-pyrazin-2-yl-amine

HRID 1951177Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]2[S:12][C:11]([NH:13][C:14]3[CH:19]=[N:18][CH:17]=[CH:16][N:15]=3)=[N:10][C:9]=2[CH3:20])[CH:5]=[CH:4][N:3]=1.[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O>[N:21]1([C:2]2[CH:7]=[C:6]([C:8]3[S:12][C:11]([NH:13][C:14]4[CH:19]=[N:18][CH:17]=[CH:16][N:15]=4)=[N:10][C:9]=3[CH3:20])[CH:5]=[CH:4][N:3]=2)[CH:25]=[CH:24][N:23]=[CH:22]1

Participants

Conditions

Temperature: 140 °C

Procedure

A stirred solution of [5-(2-Chloro-pyridin-4-yl)-4-methyl-thiazol-2-yl]-pyrazin-2-yl-amine (Ex. 2b, 0.4 g, 1.32 mmol) in DMSO (10 ml) is treated with imidazole (0.18 g, 2.64 mmol) followed by caesium carbonate (0.86 g, 2.64 mmol). The reaction mixture is heated to 140° C. for 48 hours and then allowed to cool to room temperature. The mixture is diluted with water (100 ml) and extracted with ethyl acetate (4×100 ml). The organics are combined, dried over MgSO4 and the solvent removed in vacuo to yield the crude product as a yellow oil. Purification by chromatography on silica, eluting with ethyl acetate-methanol (9:1) affords the titled compound.

Workup

temperatureto cool to room temperature
extractionextracted with ethyl acetate (4×100 ml)
dry with materialdried over MgSO4
customthe solvent removed in vacuo
customto yield the crude product as a yellow oil
customPurification by chromatography on silica
washeluting with ethyl acetate-methanol (9:1)

Sources & evidence

ORD record: ord-836e663510a7495d90d78c935f503d1f
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404684B2

Reaction notes

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