4-Fluoro-2-(trifluoromethyl)benzoyl chloride → Ethyl 2-{[4-fluoro-2-(trifluoromethyl)benzoyl]amino}-4,4,6,6-tetramethyl-4,6-dihydrothieno[2,3-c]furan-3-carboxylate

HRID 1015608Notes

Reaction equation

HRID 1015608 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:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[C:22]([C:29]([F:32])([F:31])[F:30])[CH:21]=1>>[F:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH:18][C:7]2[S:8][C:9]3[C:10]([CH3:17])([CH3:16])[O:11][C:12]([CH3:15])([CH3:14])[C:13]=3[C:6]=2[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:25])=[C:22]([C:29]([F:30])([F:31])[F:32])[CH:21]=1

Participants

3

Reactant 2

HCID 6056804-Fluoro-2-(trifluoromethyl)benzoyl chlorideHCID 673006372-Amino-4,4,6,6-tetramethyl-4,6-dihydrothieno[2,3-c]furan-3-carboxylic acid ethyl ester

Product 1

HCID 24772743Ethyl 2-{[4-fluoro-2-(trifluoromethyl)benzoyl]amino}-4,4,6,6-tetramethyl-4,6-dihydrothieno[2,3-c]furan-3-carboxylate

Procedure

The title compound was prepared from the product of Example 18A and commercially available 4-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), 1.49 (s, 6H), 1.54 (s, 6H), 4.30 (q, J=7.1 Hz, 2H), 7.76 (ddd, J=9.1, 8.6, 2.4 Hz, 1H), 7.88 (dd, J=9.3, 2.5 Hz, 1H), 7.96 (dd, J=8.6, 5.3 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, 54.84; H, 4.60; N, 3.02.

Sources & evidence

ORD record
ord-1d11c663a2e043d9937b32e8b22cf101
Source dataset
uspto-grants-2011_07
Patent number
US07985768B2

Reaction notes

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