2-Fluoro-6-(trifluoromethyl)benzoyl chloride → 2-fluoro-N-[3-(2-furoyl)-5,6,7,8-tetrahydro-4H-5,8-epoxycyclohepta[b]thien-2-yl]-6-(trifluoromethyl)benzamide

HRID 1908930Notes

Reaction equation

HRID 1908930 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]([C:15]1[O:16][CH:17]=[CH:18][CH:19]=1)=[O:14])[CH2:9][CH2:8]3.[F:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[C:22]=1[C:23](Cl)=[O:24]>>[F:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:31])([F:32])[F:33])[C:22]=1[C:23]([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]([C:15]1[O:16][CH:17]=[CH:18][CH:19]=1)=[O:14])[CH2:9][CH2:8]3)=[O:24]

Participants

3

Reactant 2

HCID 1454582-Fluoro-6-(trifluoromethyl)benzoyl chlorideHCID 66846138(2-amino-5,6,7,8-tetrahydro-4H-5,8-epoxycyclohepta[b]thien-3-yl)(2-furyl)methanone

Product 1

HCID 250074062-fluoro-N-[3-(2-furoyl)-5,6,7,8-tetrahydro-4H-5,8-epoxycyclohepta[b]thien-2-yl]-6-(trifluoromethyl)benzamide

Procedure

The title compound was prepared from the product of Example 15A and commercially available 2-fluoro-6-trifluoromethyl-benzoyl chloride according to the procedure described for Example 1C. 1H NMR (CDCl3, 300 MHz) δ 1.63-1.71 (m, 1H), 2.13-2.17 m, 4H), 3.26 (dd, J=16.3, 5.1 Hz, 1H), 4.71 (dd, J=4.9, 4.9 Hz, 1H), 5.14-5.15 (m, 1H), 6.58-6.60 (m, 1H), 7.16-7.17 (m, 1H), 7.35-7.41 (m, 1H), 7.55-7.64 (m, 3H), 11.13 (br s, 1H); MS (ESI+) m/z 466 (M+H)+.

Sources & evidence

ORD record
ord-8006c23cd7f74f8a9d23e8a7ce2d9681
Source dataset
uspto-grants-2013_12
Patent number
US08598224B2

Reaction notes

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