Potassium Carbonate → 3-{5-[3-(2-Methoxy-ethoxy)-phenyl]-pyridin-2-yloxy}-azetidine-1-carboxylic acid pyridin-3-ylamide

HRID 1469367Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([N:16]2[CH2:19][CH:18]([O:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([OH:33])[CH:28]=4)=[CH:23][N:22]=3)[CH2:17]2)=[O:15])[CH:8]=1.[CH3:34][O:35][CH2:36][CH2:37]Br>CN(C=O)C>[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([N:16]2[CH2:19][CH:18]([O:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH2:37][CH2:36][O:35][CH3:34])[CH:28]=4)=[CH:23][N:22]=3)[CH2:17]2)=[O:15])[CH:8]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Potassium carbonate (23 mg, 165 μmol) was added to a solution of 3-[5-(3-hydroxy-phenyl)-pyridin-2-yloxy]-azetidine-1-carboxylic acid pyridin-3-ylamide (20 mg 55 μmol), in DMF (0.5 mL). 2-Bromoethyl methyl ether (6 μL, 66 μmol) was added and the reaction mixture was heated to 100° C. in microwave synthesiser for 1 hr. The reaction mixture was allowed to cool and solvent removed in vacuo. The crude product was purified by preparative HPLC to afford the title product as a colourless solid (6.7 mg, 29%).

Workup

temperatureto cool
customsolvent removed in vacuo
customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record: ord-0a1376d00c0844579f4a46e0573db506
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006269B2

Reaction notes

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