Trifluoroacetic acid → HCID 54767065, compound

HRID 2045959Notes

Reaction equation

[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH2:11][C:10]([C:16]3[CH:21]=[C:20]([Cl:22])[C:19]([Cl:23])=[C:18]([Cl:24])[CH:17]=3)([C:12]([F:15])([F:14])[F:13])[O:9][N:8]=2)[O:4][C:3]=1[CH:25]=O.[CH:27]1([C:30]([NH2:32])=[O:31])[CH2:29][CH2:28]1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH2:11][C:10]([C:16]3[CH:17]=[C:18]([Cl:24])[C:19]([Cl:23])=[C:20]([Cl:22])[CH:21]=3)([C:12]([F:14])([F:13])[F:15])[O:9][N:8]=2)[O:4][C:3]=1[CH2:25][NH:32][C:30]([CH:27]1[CH2:29][CH2:28]1)=[O:31]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 3-methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-2-carbaldehyde (100 mg), cyclopropanecarboxamide (61 mg), trifluoroacetic acid (54 μl) and triethylsilane (112 μl) in toluene (2 ml) is refluxed at 110° C. After 4 hours 30 minutes the reaction mixture is concentrated in vacuo. The crude product is purified on a semi-preparative HPLC to yield cyclopropanecarboxylic acid {3-methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-2-ylmethyl}-amide (91 mg, compound 3.1 in Table 3) as a white solid. MS (HPLC/MS): 495 (MH+). Retention time: 2.08 min.

Workup

concentrationAfter 4 hours 30 minutes the reaction mixture is concentrated in vacuo
customThe crude product is purified on a semi-preparative HPLC

Sources & evidence

ORD record: ord-fd94b0cfe3784b01baad5d3d8bd9b4cc
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592418B2

Reaction notes

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