Trifluoroacetic acid → HCID 71559364, compound

HRID 2203427Notes

Reaction equation

HRID 2203427 reaction equation
[Cl:1][C:2]1[CH:36]=[CH:35][C:5]([O:6][C:7]2[C:12]([F:13])=[CH:11][C:10]([S:14]([N:17](CC3C=CC(OC)=CC=3OC)[C:18]3[S:22][N:21]=[CH:20][N:19]=3)(=[O:16])=[O:15])=[C:9]([F:34])[CH:8]=2)=[C:4]([C:37]2[N:41]3[CH:42]=[CH:43][N:44]=[CH:45][C:40]3=[CH:39][N:38]=2)[CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:36]=[CH:35][C:5]([O:6][C:7]2[C:12]([F:13])=[CH:11][C:10]([S:14]([NH:17][C:18]3[S:22][N:21]=[CH:20][N:19]=3)(=[O:15])=[O:16])=[C:9]([F:34])[CH:8]=2)=[C:4]([C:37]2[N:41]3[CH:42]=[CH:43][N:44]=[CH:45][C:40]3=[CH:39][N:38]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89555373HCID 89555373, compound

Product 1

HCID 71559364HCID 71559364, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-chloro-2-(imidazo[1,5-a]pyrazin-3-yl)phenoxy)-N-(2,4-dimethoxybenzyl)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (0.110 g, 0.16 mmol) in dichloromethane (4 mL) was added trifluoroacetic acid (0.4 mL). The mixture was stirred for 16 h at ambient temperature and concentrated in vacuo. Methanol (1 mL) was added to the residue. The mixture was concentrated in vacuo and the residue triturated in diethyl ether. The resultant solid was dissolved in a mixture of methanol and acetonitrile (1:1), filtered through a 0.2 μm filter and concentrated in vacuo. The residue was triturated in hexanes to afford 4-(4-chloro-2-(imidazo[1,5-a]pyrazin-3-yl)phenoxy)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide as a yellow solid in 90% yield (0.075 g): 1H NMR (300 MHz, DMSO-d6) δ 9.14 (s, 1H), 8.52 (s, 1H), 8.10 (d, J=4.6 Hz, 1H), 8.02 (s, 1H), 7.80 (s, 1H), 7.71-7.56 (m, 3H), 7.35 (d, J=8.9 Hz, 1H), 7.29 (dd, J=10.3, 6.2 Hz, 1H); MS (ES+) m/z 520.7 (M+1), 522.7 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. additionMethanol (1 mL) was added to the residue
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue triturated in diethyl ether
  5. dissolutionThe resultant solid was dissolved in a mixture of methanol and acetonitrile (1:1)
  6. filtrationfiltered through a 0.2 μm
  7. filtrationfilter
  8. concentrationconcentrated in vacuo
  9. customThe residue was triturated in hexanes

Sources & evidence

ORD record
ord-3d97b7aae5fa444997ce9f848a980a22
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

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