Trifluoroacetic acid → HCID 71711239, compound

HRID 528536Notes

Reaction equation

HRID 528536 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)[N:15]([CH3:42])[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)[N:15]([CH3:42])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89761344HCID 89761344, compound

Product 1

HCID 71711239HCID 71711239, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2-Chloro-4-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-4-methyl-N-(1,2,4-thiadiazol-5-yl)-1,2,3,4-tetrahydroquinoxaline-6-sulfonamide (0.046 g, 0.072 mmol) was dissolved in 1 mL of DCM and TFA (0.1 mL, 1.298 mmol) was added. The reaction was stirred for 30 minutes at room temperature. The solution 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)-4-methyl-N-(1,2,4-thiadiazol-5-yl)-1,2,3,4-tetrahydroquinoxaline-6-sulfonamide as a light pink solid. 1H NMR (400 MHz, DMSO-d6) δ=8.41 (s, 1 H), 8.02 (d, J=1.8 Hz, 1 H), 7.82 (dd, J=1.8, 8.7 Hz, 1 H), 7.67 (d, J=8.1 Hz, 1 H), 6.91 (qd, J=2.2, 4.4 Hz, 2 H), 6.03 (d, J=8.9 Hz, 1 H), 3.71 (t, J=4.8 Hz, 2 H), 3.40 (t, J=4.8 Hz, 2 H), 2.91 (s, 3H). m/z (ESI) 489.8 (M+H)+.

Workup

  1. concentrationThe solution 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-139e8af876444494a1ad1c3f3c7e179a
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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