Potassium Carbonate → HCID 86695567, compound

HRID 1425768Notes

Reaction equation

Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:27])[CH2:10][N:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][N:20]=3)=[CH:13][C:12]2=[O:26])=[C:5]([CH3:28])[CH:4]=1.Cl.[OH:30][CH2:31][C@H:32]1[CH2:37][CH2:36][CH2:35][CH2:34][NH:33]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][O:17][C:14]2[CH:15]=[CH:16][N:11]([CH2:10][C:9]([C:6]3[CH:7]=[CH:8][C:3]([CH2:2][N:33]4[CH2:34][CH2:35][CH2:36][CH2:37][C@@H:32]4[CH2:31][OH:30])=[CH:4][C:5]=3[CH3:28])=[O:27])[C:12](=[O:26])[CH:13]=2)=[N:20][CH:21]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-[2-(4-bromomethyl-2-methyl-phenyl)-2-oxo-ethyl]-4-(5-bromo-pyridin-2-ylmethoxy)-1H-pyridin-2-one (preparation 4b, 100 mg, 0.20 mmol) in DMF (2 mL) is added (R)-2-hydroxymethylpiperidine hydrochloride (75 mg, 0.50 mmol) and K2CO3 (55 mg, 0.40 mmol). The reaction mixture is stirred 2 h at 80° C. The mixture is purified via reverse phase HPLC chromatography (Phenomenex Gemini-C18 10 μm, gradient 5%→90% acetonitrile in water+0.3% NH4OH, 120 mL/min).

Workup

customThe mixture is purified via reverse phase HPLC chromatography (Phenomenex Gemini-C18 10 μm, gradient 5%→90% acetonitrile in water+0.3% NH4OH, 120 mL/min)

Sources & evidence

ORD record: ord-6027e71b9d6044b8a5f09b8d0e6ba9ce
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933079B2

Reaction notes

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