Triethylamine → HCID 178427206, compound

HRID 1507469Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH:11][C:12]([C:14]2[CH:18]=[C:17]([CH3:19])[O:16][C:15]=2[C:20]([F:23])([F:22])[F:21])=[O:13])=S)[CH:5]=[CH:6][CH:7]=1.[CH:24]1([NH2:31])[CH2:29][CH2:28][CH2:27][CH:26]([NH2:30])[CH2:25]1.C(N(CC)CC)C>CC#N.CO>[NH2:30][CH:26]1[CH2:27][CH2:28][CH2:29][CH:24]([NH:31][C:9]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)=[N:11][C:12]([C:14]2[CH:18]=[C:17]([CH3:19])[O:16][C:15]=2[C:20]([F:23])([F:22])[F:21])=[O:13])[CH2:25]1

Participants

Conditions

Temperature: 65 °C

Procedure

N-((3-Fluorophenyl)carbamothioyl)-5-methyl-2-(trifluoromethyl)furan-3-carboxamide (1.40 g, 4.05 mmol) and cyclohexane-1,3-diamine (1.38 g, 12.1 mmol) were combined in MeCN (20 mL). Triethylamine (0.818 g, 8.10 mmol), NaBiO3 (1.13 g, 4.05 mmol), and BiI3 (0.119 g, 0.203 mmol) were then added and the reaction was heated to 65° C. for 16 hours. When the reaction was complete, the solution was cooled and diluted with MeOH. Then, the resulting mixture was filtered through celite and the filtrate evaporated. The residue was re-dissolved in EtOAc and washed with water, brine, and dried over MgSO4. The organic solvent was then evaporated in vacuo to yield 1.36 g (79%) of the title compound. LCMS (ESI): calc.=426; obs. M+H=427.3 (2 overlapping peaks in ˜2:1 ratio).

Workup

temperaturethe solution was cooled
filtrationThen, the resulting mixture was filtered through celite
customthe filtrate evaporated
dissolutionThe residue was re-dissolved in EtOAc
washwashed with water, brine
dry with materialdried over MgSO4
customThe organic solvent was then evaporated in vacuo

Sources & evidence

ORD record: ord-7bd83584581c4469a306e9fa4d989cf9
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221814B2

Reaction notes

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