Trifluoroacetic acid → HCID 178527556, compound

HRID 2203442Notes

Reaction equation

HRID 2203442 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH:44]=[C:43]([Cl:45])[CH:42]=[CH:41][C:11]=3[O:12][C:13]3[C:18]([F:19])=[CH:17][C:16]([S:20]([N:23](CC4C=CC(OC)=CC=4OC)[C:24]4[S:28][N:27]=[CH:26][N:25]=4)(=[O:22])=[O:21])=[C:15]([F:40])[CH:14]=3)=[CH:9][C:4]=2[N:3]=[CH:2]1.FC(F)(F)C(O)=O>ClCCl>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH:44]=[C:43]([Cl:45])[CH:42]=[CH:41][C:11]=3[O:12][C:13]3[C:18]([F:19])=[CH:17][C:16]([S:20]([NH:23][C:24]4[S:28][N:27]=[CH:26][N:25]=4)(=[O:21])=[O:22])=[C:15]([F:40])[CH:14]=3)=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178491032HCID 178491032, compound

Product 1

HCID 178527556HCID 178527556, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(2-(1H-benzo[d]imidazol-5-yl)-4-chlorophenoxy)-N-(2,4-dimethoxybenzyl)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (0.149 g, 0.22 mmol) in dichloromethane (5 mL) was added trifluoroacetic acid (1 mL) at 0° C. The reaction mixture was stirred for 2 h at 0° C. The mixture was concentrated in vacuo and the residue was suspended in methanol (20 mL) and filtered. The filtrate was concentrated in vacuo and the residue triturated in diethyl ether (5 mL) and suspended in water (2 mL). Lyophilization affored 4-(2-(1H-benzo[d]imidazol-5-yl)-4-chlorophenoxy)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzene-sulfonamide as the corresponding beige trifluoroacetate salt in 75% yield (0.11 g): 1H NMR (300 MHz, DMSO-d6) δ9.11 (s, 1H), 8.37 (s, 1H), 7.84 (s, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.64 (dd, J=10.2, 6.5 Hz, 1H), 7.62 (d, J=2.6 Hz, 1H), 7.54 (d, J=8.3 Hz, 1H), 7.49 (dd, J=8.7, 2.5 Hz, 1H), 7.27 (d, J=8.7 Hz, 1H), 7.11 (dd, J=10.4, 6.5 Hz, 1H), (NH not observed); 19F NMR (282 MHz, DMSO-d6) δ−76.6 (s, 3F), −113.0 (d, J=15.8 Hz, 1F), −139.0 (d, J=15.9 Hz, 1F); MS (ES+) m/z 519.7 (M+1), 521.7 (M+1).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue triturated in diethyl ether (5 mL)

Sources & evidence

ORD record
ord-c559a78a92c24778b514146ceeeb32f6
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

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