Potassium Carbonate → 3-{[5-(azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-N-(1,5-dimethyl-1H-pyrazol-3-yl)-5-{[2-fluoro-1-(fluoromethyl)ethyl]oxy}benzamide

HRID 1990233Notes

Reaction equation

[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][C:4]([NH:8][C:9](=[O:23])[C:10]2[CH:15]=[C:14]([OH:16])[CH:13]=[C:12]([O:17][CH:18]([CH2:21][F:22])[CH2:19][F:20])[CH:11]=2)=[N:3]1.C(=O)([O-])[O-].[K+].[K+].[N:30]1([C:34]([C:36]2[CH:37]=[C:38]([Cl:43])[C:39](Cl)=[N:40][CH:41]=2)=[O:35])[CH2:33][CH2:32][CH2:31]1>C(#N)C>[N:30]1([C:34]([C:36]2[CH:37]=[C:38]([Cl:43])[C:39]([O:16][C:14]3[CH:15]=[C:10]([CH:11]=[C:12]([O:17][CH:18]([CH2:19][F:20])[CH2:21][F:22])[CH:13]=3)[C:9]([NH:8][C:4]3[CH:5]=[C:6]([CH3:7])[N:2]([CH3:1])[N:3]=3)=[O:23])=[N:40][CH:41]=2)=[O:35])[CH2:33][CH2:32][CH2:31]1

Participants

Conditions

Temperature: 120 °C

Procedure

A solution of N-(1,5-dimethyl-1H-pyrazol-3-yl)-3-{[2-fluoro-1-(fluoromethyl)ethyl]oxy}-5-hydroxybenzamide (0.61 mmol) in acetonitrile (5 mL), was treated with the potassium carbonate (1.23 mmol) and 5-(azetidin-1-ylcarbonyl)-2,3-dichloropyridine (0.68 mmol), before being heated to 120° C. in a microwave reactor for 4 hours. The mixture was filtered and evaporated in vacuo before being chromatographed on silica, eluting with 0-5% methanol in ethyl acetate, to give the desired compound as a white foam (175 mg).

Workup

filtrationThe mixture was filtered
customevaporated in vacuo
custombefore being chromatographed on silica
washeluting with 0-5% methanol in ethyl acetate

Sources & evidence

ORD record: ord-ec6f50b0dce046a79941f594e2dd9f01
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642259B2

Reaction notes

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