Trifluoroacetic acid → HCID 71711242, compound

HRID 528534Notes

Reaction equation

HRID 528534 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[N:12]1[C:21]2[C:16](=[CH:17][C:18]([S:22]([N:25](CC3C=CC(OC)=CC=3OC)[C:26]3[S:30][N:29]=[CH:28][N:27]=3)(=[O:24])=[O:23])=[CH:19][CH:20]=2)[NH:15][CH2:14][CH2:13]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[N:12]1[C:21]2[C:16](=[CH:17][C:18]([S:22]([NH:25][C:26]3[S:30][N:29]=[CH:28][N:27]=3)(=[O:23])=[O:24])=[CH:19][CH:20]=2)[NH:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89761773HCID 89761773, compound2×

Product 1

HCID 71711242HCID 71711242, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2-Chloro-4-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)-1,2,3,4-tetrahydroquinoxaline-6-sulfonamide (INTERMEDIATE V, 0.068 g, 0.108 mmol) was dissolved in 1 mL of DCM and TFA (0.1 mL, 1.298 mmol) was added. The reaction was stirred for 10 minutes. The material was concentrated, dissolved in acetonitrile and loaded onto an ion exchange column (pre-wetted with acetonitrile). The column was flushed several times with acetonitrile, then the product was liberated by flushing the column several times with about 1M HCl solution in MeOH/EtOAc (made by adding acetyl chloride to a MeOH/EtOAc mixture). The second filtrate was concentrated to afford 1-(2-chloro-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)-1,2,3,4-tetrahydroquinoxaline-6-sulfonamide as a purple solid. 1H NMR (400 MHz, DMSO-d6) δ=8.42 (s, 1 H), 7.99 (s, 1 H), 7.80 (d, J=8.1 Hz, 1 H), 7.63 (d, J=8.0 Hz, 1 H), 7.01 (d, J=2.1 Hz, 1 H), 6.80 (dd, J=1.9, 8.3 Hz, 1 H), 6.08 (d, J=8.4 Hz, 1 H), 3.61 (t, J=4.0 Hz, 2 H), 3.40 (t, J=4.4 Hz, 2 H). m/z (ESI) 475.8 (M+H)+.

Workup

  1. concentrationThe material was concentrated
  2. dissolutiondissolved in acetonitrile
  3. customThe column was flushed several times with acetonitrile
  4. customby flushing the column several times with about 1M HCl solution in MeOH/EtOAc (
  5. additionby adding acetyl chloride to a MeOH/EtOAc mixture)
  6. concentrationThe second filtrate was concentrated

Sources & evidence

ORD record
ord-2f67810a249c4b0aae96cf60716977ab
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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