2-Fluoro-6-(trifluoromethyl)benzoyl chloride → 2-fluoro-N-[4-methyl-3-(tetrahydro-2H-pyran-4-ylcarbonyl)-4,6-dihydrothieno[2,3-c]furan-2-yl]-6-(trifluoromethyl)benzamide

HRID 1015594Notes

Reaction equation

HRID 1015594 reaction equation
[NH2:1][C:2]1[S:10][C:5]2[CH2:6][O:7][CH:8]([CH3:9])[C:4]=2[C:3]=1[C:11]([CH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[O:12].[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:10][C:5]2[CH2:6][O:7][CH:8]([CH3:9])[C:4]=2[C:3]=1[C:11]([CH:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1)=[O:12])=[O:23]

Participants

3

Reactant 2

HCID 1454582-Fluoro-6-(trifluoromethyl)benzoyl chlorideHCID 67300631(2-amino-4-methyl-4,6-dihydrothieno[2,3-c]furan-3-yl)(tetrahydro-2H-pyran-4-yl)methanone

Product 1

HCID 247725422-fluoro-N-[4-methyl-3-(tetrahydro-2H-pyran-4-ylcarbonyl)-4,6-dihydrothieno[2,3-c]furan-2-yl]-6-(trifluoromethyl)benzamide

Procedure

The title compound was prepared from the product of Example 52A and 2-fluoro-6-trifluoromethylbenzoyl chloride by the procedure described for Example 1B. 1H NMR (DMSO-d6, 300 MHz) δ 1.33 (d, J=6.1 Hz, 3H), 1.64-1.71 (m, 4H), 3.01-3.10 (m, 2H), 3.34-3.43 (m, 1H), 3.82-3.93 (m, 2H), 4.89-5.04 (m, 2H), 5.36-5.45 (m, 1H), 7.75-7.85 (m, 3H), 12.08 (br s, 1H). MS (ESI+) m/z 493 (M+H)+.

Sources & evidence

ORD record
ord-ee70b9955065441d89acc17754998b54
Source dataset
uspto-grants-2011_07
Patent number
US07985768B2

Reaction notes

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