Nitrogen → HCID 57951175, compound

HRID 1919797Notes

Reaction equation

[C:1]1([CH3:25])[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=3)[C:10](=[O:23])[C:9](=O)[CH2:8]2)[CH:2]=1.[CH3:26][C:27]([NH2:39])([C:29]1[CH:30]=[N:31][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:33][CH:34]=1)[CH3:28].N#N>C1(C)C=CC=CC=1>[CH3:28][C:27]([NH:39][C:9]1[C:10](=[O:23])[N:11]([C:12]2[CH:13]=[CH:14][C:15]([O:18][C:19]([F:21])([F:20])[F:22])=[CH:16][CH:17]=2)[CH:7]([C:3]2[CH:2]=[C:1]([CH3:25])[CH:6]=[CH:5][CH:4]=2)[CH:8]=1)([C:29]1[CH:30]=[N:31][C:32]([C:35]([F:37])([F:38])[F:36])=[CH:33][CH:34]=1)[CH3:26]

Participants

Conditions

Temperature: 80 °C

Procedure

Charge toluene (20 mL) to a flask containing (±)-5-m-tolyl-1-(4-trifluoromethoxy-phenyl)-pyrrolidine-2,3-dione (4.13 g; 11.82 mmol). Add 1-methyl-1-(6-trifluoromethyl-pyridin-3-yl)-ethylamine (4.83 g, 23.65 mmol) to the above solution in an atmosphere of N2. Heat the reaction mixture to 80° C. for 24 hours. Cool to ambient temperature and evaporate in vacuo. Dissolve in MeOH (90 mL) and pass through an SCX-2 ion exchange resin cartridge. Evaporate the MeOH wash to give the crude product. Purify on an SCX-2 ion exchange resin cartridge (eluent with methanol) and then by chromatography on a silica gel column eluting with iso-hexane/ethyl acetate (80:20) to afford the titled compound (2.54 g, 58%). MS (m/z): 536.1 (M+1).

Workup

temperatureCool to ambient temperature
customevaporate in vacuo
dissolutionDissolve in MeOH (90 mL)
customEvaporate the MeOH
washwash
customto give the crude product
customPurify on an SCX-2 ion exchange resin cartridge (eluent with methanol)
washby chromatography on a silica gel column eluting with iso-hexane/ethyl acetate (80:20)

Sources & evidence

ORD record: ord-9b0a1fcdab7a4616a416385c29c7f1d1
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08168659B2

Reaction notes

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