Trifluoroacetic acid → HCID 86687557, compound

HRID 1473500Notes

Reaction equation

HRID 1473500 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[C:13]1[C:22]2[C:17](=[CH:18][C:19]([S:23]([N:26](CC3C=CC(OC)=CC=3)[C:27]3[S:28][CH:29]=[CH:30][N:31]=3)(=[O:25])=[O:24])=[CH:20][CH:21]=2)[C:16](=[O:41])[NH:15][N:14]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[C:13]1[C:22]2[C:17](=[CH:18][C:19]([S:23]([NH:26][C:27]3[S:28][CH:29]=[CH:30][N:31]=3)(=[O:25])=[O:24])=[CH:20][CH:21]=2)[C:16](=[O:41])[NH:15][N:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86687555HCID 86687555, compound

Product 1

HCID 86687557HCID 86687557, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2-Methoxy-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-4-oxo-N-(thiazol-2-yl)-3,4-dihydrophthalazine-6-sulfonamide (40 mg, 0.066 mmol) was dissolved in DCM (664 μl) and then TFA (25.6 μl, 0.332 mmol) was added at RT. After stirring for 30 min, the reaction was quenched with saturated aqueous NaHCO3 (1 mL). A white solid precipitated out of the solution and was filtered off with the aid of water. The solid was washed with 3 mL of water and dried to afford the product 1-(2-methoxy-4-(trifluoromethyl)phenyl)-4-oxo-N-(thiazol-2-yl)-3,4-dihydrophthalazine-6-sulfonamide (16 mg, 50% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 3.78 (s, 3H), 6.83 (d, J=4.38 Hz, 1H), 7.24 (d, J=4.49 Hz, 1H), 7.41-7.53 (m, 3H), 7.60 (d, J=7.80 Hz, 1H), 8.15 (dd, J=8.49, 1.87 Hz, 1H), 8.63 (d, J=1.82 Hz, 1H), 13.10 (s, 1H). m/z (ESI) 483.0 (M+H)+.

Workup

  1. customthe reaction was quenched with saturated aqueous NaHCO3 (1 mL)
  2. customA white solid precipitated out of the solution
  3. filtrationwas filtered off with the aid of water
  4. washThe solid was washed with 3 mL of water
  5. customdried

Sources & evidence

ORD record
ord-63ff689e3e64444099b0241b9c2a0fb7
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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