2-(Trifluoromethyl)benzoyl chloride → propyl 2-{[2-(trifluoromethyl)benzoyl]amino}-5,6,7,8-tetrahydro-4H-5,8-epoxycyclohepta[b]thiophene-3-carboxylate

HRID 252429Notes

Reaction equation

HRID 252429 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]([F:31])([F:30])[C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24]>>[F:19][C:20]([F:30])([F:31])[C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][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]([O:15][CH2:16][CH2:17][CH3:18])=[O:14])[CH2:9][CH2:8]3)=[O:24]

Participants

3

Reactant 2

HCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 66846079propyl 2-amino-5,6,7,8-tetrahydro-4H-5,8-epoxycyclohepta[b]thiophene-3-carboxylate

Product 1

HCID 25003090propyl 2-{[2-(trifluoromethyl)benzoyl]amino}-5,6,7,8-tetrahydro-4H-5,8-epoxycyclohepta[b]thiophene-3-carboxylate

Procedure

The title compound was prepared from the product of Example 34A and commercially available 2-trifluoromethyl-benzoyl chloride according to the procedure described for Example 1C. 1H NMR (DMSO-d6, 300 MHz) δ 0.92 (t, J=7.5Hz, 3H), 1.64-1.71 (m, 3H), 1.98-2.15 (m, 3H), 2.58 (d, J=17.0Hz, 1H), 3.11 (dd, J=16.6, 4.4Hz, 1H), 4.16 (t, J=6.4 Hz, 2H), 4.69-4.74 (m, 1H), 5.14-5.16 (m, 1H), 7.80-7.94 (m, 4H), 11.40 (br s, 1H); MS (ESI+) m/z 440 (M+H)+. Anal. calcd. for C21H20F3NO4S: C, 57.40; H, 4.59; N; 3.19. Found: C, 57.44; H, 4.47; N, 3.14.

Sources & evidence

ORD record
ord-9e011653ff594bf586bd370d373066c7
Source dataset
uspto-grants-2011_01
Patent number
US07868038B2

Reaction notes

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