Trifluoroacetic acid → HCID 86687733, compound

HRID 1473659Notes

Reaction equation

HRID 1473659 reaction equation
COC1C=CC(C[N:8]([C:31]2[S:35][N:34]=[CH:33][N:32]=2)[S:9]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[O:28][CH3:29])=[N:17][NH:16][C:15]3=[O:30])(=[O:11])=[O:10])=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:29][O:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:18]1[C:19]2[C:14](=[CH:13][C:12]([S:9]([NH:8][C:31]3[S:35][N:34]=[CH:33][N:32]=3)(=[O:10])=[O:11])=[CH:21][CH:20]=2)[C:15](=[O:30])[NH:16][N:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86687734HCID 86687734, compound

Product 1

HCID 86687733HCID 86687733, compoundYield 21.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(4-methoxybenzyl)-1-(2-methoxyphenyl)-4-oxo-N-(1,2,4-thiadiazol-5-yl)-3,4-dihydrophthalazine-6-sulfonamide (65.0 mg, 0.121 mmol) was dissolved in DCM (1.21 mL) and then TFA (46.7 μl, 0.607 mmol) was added. After 1 d at rt, LCMS showed mainly product. The reaction was quenched with 1 mL of saturated aqueous NaHCO3 and was concentrated. Chromatography was performed using reverse phase Isolera through a pre-packed C18 column (12 g), eluting with a gradient of 0% to 60% MeCN with 1% TFA in water with 1% TFA. Fractions containing the product were combined and concentrated. White solid precipitated out of the water. The solid was filtered off with an aid of water and dried to afford 1-(2-methoxyphenyl)-4-oxo-N-(1,2,4-thiadiazol-5-yl)-3,4-dihydrophthalazine-6-sulfonamide (11 mg, 21.8% yield). m/z (ESI) 416.0 (M+H)+.

Workup

  1. customThe reaction was quenched with 1 mL of saturated aqueous NaHCO3
  2. concentrationwas concentrated
  3. washeluting with a gradient of 0% to 60% MeCN with 1% TFA in water with 1% TFA
  4. additionFractions containing the product
  5. concentrationconcentrated
  6. customWhite solid precipitated out of the water
  7. filtrationThe solid was filtered off with an aid of water
  8. customdried

Sources & evidence

ORD record
ord-d16389e1184d4908b393442d3e109e25
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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