Imidazole → N-[4-(2-Furyl)-5-morpholinothiazol-2-yl]-2-(imidazol-1-ylmethyl)pyridine-5-carboxamide

HRID 337409Notes

Reaction equation

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

Participants

Conditions

Temperature: 95 °C

Procedure

Compound 36 (97.1 mg, 0.240 mmol) was dissolved in DMF (2.5 mL), imidazole (49.0 mg, 0.721 mmol) was added thereto, followed by stirring at 95° C. for 2 hours. The reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under the reduced pressure. The resulting residue was purified through silica gel column chromatography (chloroform:methanol=17:3) to afford the entitled Compound 37 (58.0 mg, 55%).

Workup

extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with a saturated aqueous solution of sodium chloride
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent was distilled away under the reduced pressure
customThe resulting residue was purified through silica gel column chromatography (chloroform:methanol=17:3)

Sources & evidence

ORD record: ord-609c66b190ca405e8723a6754be28c4c
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889718B2

Reaction notes

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