Hydrochloric Acid → HCID 86652693, compound

HRID 2095523Notes

Reaction equation

[C:1]([O:5][C:6](=[O:18])[CH2:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][NH:13][C@@H:12]([CH3:16])[C:11]1=[O:17])([CH3:4])([CH3:3])[CH3:2].Cl.I[C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[C:1]([O:5][C:6](=[O:18])[CH2:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][N:13]([C:26]2[CH:21]=[CH:22][C:23]([C:31]([F:32])([F:34])[F:33])=[C:24]([C:27]([F:28])([F:30])[F:29])[CH:25]=2)[C@@H:12]([CH3:16])[C:11]1=[O:17])([CH3:2])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 0.20 g (0.78 mmol) of 4-((S)-3-Methyl-2-oxo-piperazin-1-yl)-butyric acid tert-butyl ester, 0.1 eq. of HCl, 0.53 g (1.56 mmol) of 4-iodo-1,2-bis-trifluoromethyl-benzene (WO2007034282), 0.04 g (0.078 mmol) bis(tri-tert-butylphosphine)palladium(0) and 0.33 g (1.56 mmol) tripotassium phosphate in 2 ml of 1,2-dimethoxyethane was degased and heated at 120° C. for 2 h under microwave irradiation, diluted with dichloromethane, filtered and evaporated. Purification on a SiO2-column (1-propanol in n-heptane 2 to 5%), gave the titled compound in 35% yield as light brown oil. MS: 413.13 (M[-C4H8]H+).

Workup

customwas degased
additiondiluted with dichloromethane
filtrationfiltered
customevaporated
customPurification on a SiO2-column (1-propanol in n-heptane 2 to 5%)

Sources & evidence

ORD record: ord-3ed51bd2537f4fc99c961292ede3ddc2
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445674B2

Reaction notes

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