Potassium Carbonate → HCID 67004780, compound

HRID 563150Notes

Reaction equation

[CH2:1]([C@H:8]([N:24]([CH2:39][C:40]1[CH:41]=[N:42][C:43](Br)=[CH:44][CH:45]=1)[C:25](=[O:38])[CH:26]=[CH:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=1)[C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:47]1[CH2:51][CH2:50][CH2:49][C:48]1=[O:52].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.[Cu]I>[CH2:1]([C@H:8]([N:24]([CH2:39][C:40]1[CH:41]=[N:42][C:43]([N:47]2[CH2:51][CH2:50][CH2:49][C:48]2=[O:52])=[CH:44][CH:45]=1)[C:25](=[O:38])[CH:26]=[CH:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=1)[C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

In an inert atmosphere, N—[(S)-1-benzyl-2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-N-(6-bromo-pyridin-3-ylmethyl)-3-(4-trifluoromethyl-phenyl)-acrylamide (70 mg, 0.101 mmol), 2-pyrrolidinon (10.3 mg, 0.121 mmol), potassium carbonate (27.9 mg, 0.202 mmol), copper(I)iodide (1 mg, 0.005 mmol) and N,N-dimethylenediamine (1 mg, 0.01 mmol) were dissolved in dioxane (1 mL). The reaction mixture was heated to 120° C. for 12 h, then filtered over a plug of silicagel with EtOAc, concentrated and purified by perp. HPLC to give 29 mg (52%) of N—[(S)-1-benzyl-2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-N-[6-(2-oxo-pyrrolidin-1-yl)-pyridin-3-ylmethyl]-3-(4-trifluoromethyl-phenyl)-acrylamide. (LC-MS: tR=1.02 min; [M+H]+=688.46).

Workup

filtrationfiltered over a plug of silicagel with EtOAc
concentrationconcentrated
custompurified by perp

Sources & evidence

ORD record: ord-6a58f10a75f042b0aba9dd44a1615cf8
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067419B2

Reaction notes

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