Potassium Carbonate → 2-{-4-[1-(4-Cyclopropylmethoxy-2-methoxy-phenyl)-piperidin-4-yl]-phenyl}-N-ethyl-propionamide

HRID 409736Notes

Reaction equation

[CH2:1]([NH:3][C:4](=[O:19])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1)[CH3:6])[CH3:2].Br[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH:29]2[CH2:31][CH2:30]2)=[CH:23][C:22]=1[O:32][CH3:33].C(=O)([O-])[O-].[K+].[K+].N1CCC[C@H]1C(O)=O>CS(C)=O.[Cu]I>[CH:29]1([CH2:28][O:27][C:24]2[CH:25]=[CH:26][C:21]([N:16]3[CH2:17][CH2:18][CH:13]([C:10]4[CH:11]=[CH:12][C:7]([CH:5]([CH3:6])[C:4]([NH:3][CH2:1][CH3:2])=[O:19])=[CH:8][CH:9]=4)[CH2:14][CH2:15]3)=[C:22]([O:32][CH3:33])[CH:23]=2)[CH2:30][CH2:31]1

Participants

Conditions

Temperature: 100 °C

Procedure

100 mg (0.38 mmol) N-Ethyl-2-(4-piperidin-4-yl-phenyl)-propionamide (VI.1) in 2 mL DMSO are added to a mixture of 99 mg (0.38 mmol) 1-bromo-4-cyclopropylmethoxy-2-methoxy-benzene, 106 mg (0.77 mmol) potassium carbonate, 7.3 mg (0.038 mmol) copper(I) iodide and 8.8 mg (0.077 mmol) (L)-proline under inert gas atmosphere. The mixture is stirred for 7 d at 90° C. and for additional 4 d at 100° C. After that time, the mixture is filtered and the solvent is evaporated. The residue is purified by HPLC (column: Waters XBridge 50; eluent A: water+0.3% NH4OH, eluent B: MeOH) to yield the desired product.

Workup

filtrationAfter that time, the mixture is filtered
customthe solvent is evaporated
customThe residue is purified by HPLC (column: Waters XBridge 50; eluent A: water+0.3% NH4OH, eluent B: MeOH)

Sources & evidence

ORD record: ord-0d79f3b0436d41c4ab689d99912fe452
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759528B2

Reaction notes

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