Ammonium trifluoroacetate → 3-Cyclopropyl-5-pyridin-3-yl-2-(4-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid ethyl ester

HRID 545341Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:31])[CH:5]([N:14]([CH:28]1[CH2:30][CH2:29]1)[C:15](=O)[C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=1)[C:6](=O)[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[CH3:2].FC(F)(F)C([O-])=O.[NH4+:39]>CCO>[CH2:1]([O:3][C:4]([C:5]1[N:14]([CH:28]2[CH2:30][CH2:29]2)[C:15]([C:16]2[CH:17]=[CH:18][C:19]([O:22][C:23]([F:25])([F:26])[F:24])=[CH:20][CH:21]=2)=[N:39][C:6]=1[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=[O:31])[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

To 1.2 g (3 mmol) of 2-[cyclopropyl-(4-trifluoromethoxy-benzoyl)-amino]-3-oxo-3-pyridin-3-yl-propionic acid ethyl ester in 10 ml of EtOH was added 1.4 g (11 mmol) of ammonium trifluoroacetate. The EtOH was evaporated and the residue heated to 110° C. for 4 h. The cooled residue was partitioned between saturated sodium hydrogen carbonate solution and CH2Cl2. The organic phase was dried with sodium sulfate and concentrated. Purification by flash column chromatography [n-heptane/EtOAc 3:7 to 1:1] afforded 0.9 g (80%) of the title compound as a colorless solid. MS: 418.2 (MH+).

Workup

customThe EtOH was evaporated
customThe cooled residue was partitioned between saturated sodium hydrogen carbonate solution and CH2Cl2
dry with materialThe organic phase was dried with sodium sulfate
concentrationconcentrated
customPurification by flash column chromatography [n-heptane/EtOAc 3:7 to 1:1]

Sources & evidence

ORD record: ord-b0a82083842f42729063092905c2c2fd
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935707B2

Reaction notes

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