2-Fluoro-6-(trifluoromethyl)benzoyl chloride → propyl 2-{[2-fluoro-6-(trifluoromethyl)benzoyl]amino}-5,6,7,8-tetrahydro-4H-5,8-epoxycyclohepta[b]thiophene-3-carboxylate
Reaction equation
[NH2:1][C:2]1[S:6][C:5]2[CH:7]3[O:12][CH:10]([CH2:11][C:4]=2[C:3]=1[C:13]([O:15][CH2:16][CH2:17][CH3:18])=[O:14])[CH2:9][CH2:8]3.[F:19][C:20]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[C:21]=1[C:22](Cl)=[O:23]>>[F:19][C:20]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:30])([F:31])[F:32])[C:21]=1[C:22]([NH:1][C:2]1[S:6][C:5]2[CH:7]3[O:12][CH:10]([CH2:11][C:4]=2[C:3]=1[C:13]([O:15][CH2:16][CH2:17][CH3:18])=[O:14])[CH2:9][CH2:8]3)=[O:23]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared from the product of Example 34A and commercially available 2-fluoro-6-trifluoromethyl-benzoyl chloride according to the procedure described for Example 1C. 1H NMR (DMSO-d6, 300 MHz) δ0.92 (t, J=7.1Hz, 3H), 1.60-1.72 (m, 3H), 1.98-2.17 (m, 3H), 2.57 (d, J=17.0Hz, 1H), 3.10 (dd, J=17.1, 4.9Hz, 1H), 4.15 (t, J=6.4 Hz, 2H), 4.69-4.73 (m, 1H), 5.14-5.16 (m, 1H), 7.73-7.87 (m, 3H), 11.53 (br s, 1H); MS (ESI+) m/z 458 (M+H)+. Anal. calcd. for C21H19F4NO4S: C, 55.14; H, 4.19; N; 3.06. Found: C, 55.19; H, 3.99; N, 3.08.
Sources & evidence
- ORD record
- ord-c3e1984b0a644284bcf16d0ce5a95308
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07868038B2
Reaction notes
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