Potassium Carbonate → (S)-N-(1-{4-[1-(2-Cyano-4-propoxy-phenyl)-piperidin-4-yl]-phenyl}-ethyl)-acetamide

HRID 1470755Notes

Reaction equation

N1CCC([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C@@H:13]([NH:15][C:16](=[O:18])[CH3:17])[CH3:14])CC1.Br[C:20]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH3:31])=[CH:24][C:21]=1[C:22]#[N:23].C(=O)([O-])[O-].[K+].[K+].[NH:38]1[CH2:45][CH2:44][CH2:43][C@H:39]1[C:40](O)=O>CS(C)=O.[Cu]I.O>[C:22]([C:21]1[CH:24]=[C:25]([O:28][CH2:29][CH2:30][CH3:31])[CH:26]=[CH:27][C:20]=1[N:38]1[CH2:45][CH2:44][CH:43]([C:11]2[CH:10]=[CH:9][C:8]([C@@H:13]([NH:15][C:16](=[O:18])[CH3:17])[CH3:14])=[CH:7][CH:12]=2)[CH2:39][CH2:40]1)#[N:23]

Participants

Conditions

Temperature: 90 °C

Procedure

100 mg (0.41 mmol) (S)—N-[1-(Piperidin-4-yl-phenyl)-ethyl]-acetamide (V.1) in 2 mL DMSO are added to a mixture of 97 mg (0.41 mmol) 2-bromo-5-propoxy-benzonitrile, 112 mg (0.82 mmol) potassium carbonate, 7.7 mg (0.041 mmol) copper(I) iodide and 9 mg (0.08 mmol) (L)-proline under inert gas atmosphere. The mixture is stirred for 7 d at 90° C. After that time, water is added and the mixture is extracted with ethyl acetate. The organic layer is dried over sodium sulphate and the solvent is removed in vacuo. The residue is purified by HPLC (column: Waters XBridge 5 μM; eluent A: water+0.3% NH4OH, eluent B: MeOH) to yield the desired product.

Workup

extractionthe mixture is extracted with ethyl acetate
dry with materialThe organic layer is dried over sodium sulphate
customthe solvent is removed in vacuo
customThe residue is purified by HPLC (column: Waters XBridge 5 μM; eluent A: water+0.3% NH4OH, eluent B: MeOH)

Sources & evidence

ORD record: ord-e8983687834e4d8e8730ce889afb9dcc
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006450B2

Reaction notes

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