Trifluoroacetic acid → HCID 42600592, compound

HRID 661357Notes

Reaction equation

HRID 661357 reaction equation
FC(F)(F)[C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.FC(F)(F)S(O[C:18]1[CH2:23][CH2:22][C:21]([C:26]2[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][N:27]=2)([O:24][CH3:25])[CH2:20][CH:19]=1)(=O)=O.[F:35][C:36]([F:56])([F:55])[S:37](OC1CCC(C2C(Cl)=CC=CN=2)(F)CC=1)(=[O:39])=[O:38].[C:57](O)(C(F)(F)F)=[O:58]>>[Cl:32][C:31]1[C:26]([C:21]2([O:24][CH3:25])[CH2:22][CH2:23][C:18]([C:57]([NH:7][C:6]3[CH:5]=[CH:4][C:3]([S:37]([C:36]([F:56])([F:55])[F:35])(=[O:39])=[O:38])=[CH:9][CH:8]=3)=[O:58])=[CH:19][CH2:20]2)=[N:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 99644-(Trifluoromethyl)anilineHCID 86630279HCID 86630279, compoundHCID 86630280HCID 86630280, compound

Product 1

HCID 42600592HCID 42600592, compound

Procedure

The title compound was prepared using the procedure as described in Example 1E, except for substituting 4-(trifluoromethylsulfonyl)aniline for 4-(trifluoromethyl)aniline, and substituting the product of Example 7C for the product of Example 1D. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.21-2.44 (m, 4H), 2.90 (s, 2H), 2.96 (s, 3H), 6.81 (t, J=3.90 Hz, 1H), 7.42 (dd, J=8.14, 4.41 Hz, 1H), 7.95 (dd, J=7.97, 1.52 Hz, 1H), 8.06 (d, J=9.16 Hz, 2H), 8.14 (d, J=9.16 Hz, 2H), 8.53 (dd, J=4.75, 1.35 Hz, 1H), 10.39 (s, 1H). MS (ESI) m/z 475.02 (M+H)+. Calcd for C20H18ClF3N2O4S.0.16 TFA: C, 49.49, H, 3.71, N, 5.68; Found: C, 49.57, H, 3.57, N, 5.42.

Sources & evidence

ORD record
ord-6e84c5a7ad51404bb9de91f048ff3b22
Source dataset
uspto-grants-2011_12
Patent number
US08084616B2

Reaction notes

Loading…