Potassium Carbonate → 2-{4-[1-(2-Cyano-4-cyclopropylmethoxy-phenyl)-piperidin-4-yl]-phenyl}-N-cyclopropyl-propionamide

HRID 409737Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH:7]1([NH:10][C:11](=[O:26])[CH:12]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)=[CH:16][CH:15]=2)[CH3:13])[CH2:9][CH2:8]1.[CH:27]1([CH2:30][O:31][C:32]2[CH:33]=[CH:34][C:35](F)=[C:36]([CH:39]=2)[C:37]#[N:38])[CH2:29][CH2:28]1>CC(N(C)C)=O>[C:37]([C:36]1[CH:39]=[C:32]([O:31][CH2:30][CH:27]2[CH2:29][CH2:28]2)[CH:33]=[CH:34][C:35]=1[N:23]1[CH2:22][CH2:21][CH:20]([C:17]2[CH:18]=[CH:19][C:14]([CH:12]([CH3:13])[C:11]([NH:10][CH:7]3[CH2:8][CH2:9]3)=[O:26])=[CH:15][CH:16]=2)[CH2:25][CH2:24]1)#[N:38]

Participants

Conditions

Temperature: 150 °C

Procedure

101 mg (0.73 mmol) potassium carbonate are added to a mixture of 80 mg (0.29 mmol) N-cyclopropyl-2-(4-piperidin-4-yl-phenyl)-propionamide (XI.1) and 56 mg (0.29 mmol) 5-cyclopropylmethoxy-2-fluoro-benzonitrile (1.8) in 2 mL DMA. The mixture is stirred for 6 h at 150° C. under microwave irradiation. Subsequently the solvent is removed in vacuo and the residue is purified using reversed phase HPLC (water, 0.3% NH4OH/MeOH) to yield the desired product.

Workup

customSubsequently the solvent is removed in vacuo
customthe residue is purified

Sources & evidence

ORD record: ord-18f28cf08b77456fbf0cf7c242c472ea
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759528B2

Reaction notes

Loading…