Acetyl chloride → {2-[4-Methoxy-4-(methoxycarbonyl)piperidin-1-yl]pyrimidin-5-yl}boronic acid

HRID 626958Notes

Reaction equation

[C:1]([Cl:4])(=O)C.C(O[C:10]([N:12]1[CH2:17][CH2:16][C:15]([O:21][CH3:22])([C:18]([OH:20])=[O:19])[CH2:14][CH2:13]1)=O)(C)(C)C.C(=O)([O-])[O-].[Na+].[Na+].ClC1[N:35]=[CH:34][C:33]([B:36]([OH:38])[OH:37])=[CH:32][N:31]=1>CO.C(O)C>[ClH:4].[CH3:22][O:21][C:15]1([C:18]([O:20][CH3:1])=[O:19])[CH2:14][CH2:13][N:12]([C:10]2[N:35]=[CH:34][C:33]([B:36]([OH:38])[OH:37])=[CH:32][N:31]=2)[CH2:17][CH2:16]1

Participants

Conditions

Temperature: 60 °C

Procedure

A 2% solution of HCl in MeOH was prepared by adding acetyl chloride (1.1 mL) to MeOH (25 mL). To this solution was added 1-[(tert-butoxy)carbonyl]-4-methoxypiperidine-4-carboxylic acid (1 g, 3.6637 mmol) and the solution was heated under reflux for 6 h. The reaction mixture was evaporated to dryness and left on a vacuum line for 30 minutes. The material thus obtained was dissolved in ethanol (8 mL) and stirred with sodium carbonate (0.96 g, 9.1 mmol) for 10 minutes, then (2-chloropyrimidin-5-yl)-boronic acid (0.57 g, 3.61 mmol) was added and the mixture was stirred at 60° C. for 6 h. The reaction mixture was filtered through celite and the solvents removed in vacuo to give the title compound (0.8 g, 71%) as a white foam, which was used without further purification. LCMS (pH 10) MH+ 296, RT 0.86 minutes.

Workup

temperaturethe solution was heated
temperatureunder reflux for 6 h
customThe reaction mixture was evaporated to dryness
customThe material thus obtained
filtrationThe reaction mixture was filtered through celite
customthe solvents removed in vacuo

Sources & evidence

ORD record: ord-d91e1fd3456c4cedaa82049b1bc8afc4
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309243B2

Reaction notes

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