5-Fluoro-2-(trifluoromethyl)benzoyl chloride → Ethyl 2-{[5-fluoro-2-(trifluoromethyl)benzoyl]amino}-4,4,6,6-tetramethyl-4,6-dihydrothieno[2,3-c]furan-3-carboxylate
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:13]2[C:12]([CH3:15])([CH3:14])[O:11][C:10]([CH3:17])([CH3:16])[C:9]=2[S:8][C:7]=1[NH2:18])=[O:5])[CH3:2].[F:19][C:20]1[CH:21]=[CH:22][C:23]([C:29]([F:32])([F:31])[F:30])=[C:24]([CH:28]=1)[C:25](Cl)=[O:26]>>[F:19][C:20]1[CH:21]=[CH:22][C:23]([C:29]([F:30])([F:31])[F:32])=[C:24]([CH:28]=1)[C:25]([NH:18][C:7]1[S:8][C:9]2[C:10]([CH3:17])([CH3:16])[O:11][C:12]([CH3:15])([CH3:14])[C:13]=2[C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:26]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared from the product of Example 18A and commercially available 5-fluoro-2-(trifluoromethyl)benzoyl chloride using the procedure described for Example 1B. 1H NMR (DMSO-d6, 300 MHz) δ 1.30 (t, J=7.1 Hz, 3H), 1.54 (s, 6H), 1.49 (s, 6H), 4.30 (q, J=7.1 Hz, 2H), 7.63-7.70 (m, 1H), 7.82 (dd, J=8.6, 2.5 Hz, 1H), 8.01 (dd, J=8.8, 5.1 Hz, 1H), 11.48 (br s, 1H). MS (ESI+) m/z 460 (M+H)+. Anal. calcd. for C21H21F4NO4S: C, 54.90; H, 4.61; N, 3.05. Found: C, 54.72; H, 4.68; N, 2.98.
Sources & evidence
- ORD record
- ord-cbec66a23a184281bb5d000f7c33bd93
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07985768B2
Reaction notes
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