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

HRID 1015604Notes

Reaction equation

HRID 1015604 reaction equation
[NH2:1][C:2]1[S:13][C:5]2[C:6]([CH3:12])([CH3:11])[O:7][C:8]([CH3:10])([CH3:9])[C:4]=2[C:3]=1[C:14]([O:16][CH2:17][CH2:18][CH3:19])=[O:15].[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:13][C:5]2[C:6]([CH3:11])([CH3:12])[O:7][C:8]([CH3:9])([CH3:10])[C:4]=2[C:3]=1[C:14]([O:16][CH2:17][CH2:18][CH3:19])=[O:15])=[O:24]

Participants

3

Reactant 2

HCID 1454582-Fluoro-6-(trifluoromethyl)benzoyl chlorideHCID 67300643Propyl 2-amino-4,4,6,6-tetramethyl-4,6-dihydrothieno[2,3-c]furan-3-carboxylate

Product 1

HCID 24772683Propyl 2-{[2-fluoro-6-(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 62A and commercially available 2-fluoro-6-(trifluoromethyl)benzoyl chloride using the procedure described for Example 1B. 1H NMR (DMSO-d6, 300 MHz) δ 0.90 (t, J=7.5 Hz, 3H), 1.49 (s, 6H), 1.54 (s, 6H), 1.62-1.74 (m, 2H), 4.20 (t, J=6.7 Hz, 2H), 7.74-7.88 (m, 3H), 11.61 (br s, 1H). MS (ESI+) m/z 474 (M+H)+. Anal. calcd. for C22H23F4NO4S: C, 55.81; H, 4.90; N, 2.96. Found: C, 56.11; H, 5.04; N, 3.01.

Sources & evidence

ORD record
ord-6d30156f5712483085124d9cab1d8aee
Source dataset
uspto-grants-2011_07
Patent number
US07985768B2

Reaction notes

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