Potassium Carbonate → HCID 178495722, compound

HRID 1990190Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([C:14]([NH:16][C:17]2[CH:21]=[CH:20][N:19](C(OC(C)(C)C)=O)[N:18]=2)=[O:15])[CH:5]=[C:6]([O:8][C@@H:9]([CH3:13])[CH2:10][O:11][CH3:12])[CH:7]=1.[N:29]1([C:33]([C:35]2[CH:36]=[CH:37][C:38](Cl)=[N:39][CH:40]=2)=[O:34])[CH2:32][CH2:31][CH2:30]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:29]1([C:33]([C:35]2[CH:36]=[CH:37][C:38]([O:1][C:2]3[CH:3]=[C:4]([CH:5]=[C:6]([O:8][C@@H:9]([CH3:13])[CH2:10][O:11][CH3:12])[CH:7]=3)[C:14]([NH:16][C:17]3[CH:21]=[CH:20][NH:19][N:18]=3)=[O:15])=[N:39][CH:40]=2)=[O:34])[CH2:32][CH2:31][CH2:30]1

Participants

Conditions

Temperature: 160 °C

Procedure

A solution of 1,1-dimethylethyl 3-{[(3-hydroxy-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}phenyl)carbonyl]amino}-1H-pyrazole-1-carboxylate (157 mg, 0.4 mmol) and 5-(azetidin-1-ylcarbonyl)-2-chloropyridine (95 mg, 0.48 mmol) in acetonitrile (2 mL), containing potassium carbonate (111 mg, 0.8 mmol), was heated in a microwave reactor at 160° C. for 6 hours. The reaction mixture was filtered and the filtrate evaporated to dryness under reduced pressure and purified by chromatography on silica, eluting with 50-100% ethyl acetate in hexane to give a product which was further purified by chromatography on silica, eluting with 0-8% methanol in ethyl acetate, to give the required product as a white foam (21 mg).

Workup

filtrationThe reaction mixture was filtered
customthe filtrate evaporated to dryness under reduced pressure
custompurified by chromatography on silica
washeluting with 50-100% ethyl acetate in hexane
customto give a product which
customwas further purified by chromatography on silica
washeluting with 0-8% methanol in ethyl acetate

Sources & evidence

ORD record: ord-d183bdc1f3ab44c485c1077938e9c72e
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642259B2

Reaction notes

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