Trifluoroacetic acid → HCID 58392128, compound

HRID 561642Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](O)([CH2:11][CH3:12])[CH2:9][CH3:10])=[C:4]([F:14])[CH:3]=1.[Cl-].[In+3].[Cl-].[Cl-].FC(F)(F)C(O)=O.[CH3:26][S:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[C:33]2[C:37]=1[NH:36][CH:35]=[CH:34]2>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:34]2[C:33]3[C:37](=[C:29]([CH2:28][S:27][CH3:26])[CH:30]=[CH:31][CH:32]=3)[NH:36][CH:35]=2)([CH2:11][CH3:12])[CH2:9][CH3:10])=[C:4]([F:14])[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

600 mg (2.77 mmol) of the compound from Example 146A, 585 mg (2.64 mmol) of indium(III) chloride and 301 mg (2.64 mmol) of trifluoroacetic acid were added to 446 mg (2.52 mmol) of the compound from Example 8A in 15 ml of dichloromethane. The reaction mixture was stirred at 80° C. for 1 h. After cooling to RT, the reaction solution was mixed with dichloromethane and silica gel, and the solvent was removed in a rotary evaporator. The residue was purified twice by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate gradient) and twice by preparative HPLC (mobile phase: acetonitrile/water gradient). 208 mg (22% of theory) of the title compound were obtained.

Workup

temperatureAfter cooling to RT
customthe solvent was removed in a rotary evaporator
customThe residue was purified twice by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate gradient) and twice by preparative HPLC (mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record: ord-6f182494c1684cf2a3dda1c7d97544b5
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063234B2

Reaction notes

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