Trifluoroacetic acid → HCID 20755350, compound

HRID 22874Notes

Reaction equation

HRID 22874 reaction equation
C([O:5][C:6](=[O:37])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[C:19](=[O:20])[C:18]3[CH:21]=[C:22]([C:25]#[C:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:23]=[CH:24][C:17]=3[N:16]([CH3:34])[S:15]2(=[O:36])=[O:35])=[CH:9][CH:8]=1)(C)(C)C.FC(F)(F)C(O)=O>>[CH3:34][N:16]1[S:15](=[O:36])(=[O:35])[N:14]([CH2:13][C:10]2[CH:9]=[CH:8][C:7]([C:6]([OH:37])=[O:5])=[CH:12][CH:11]=2)[C:19](=[O:20])[C:18]2[CH:21]=[C:22]([C:25]#[C:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:23]=[CH:24][C:17]1=2

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20755376HCID 20755376, compound

Product 1

HCID 20755350HCID 20755350, compoundYield 23.2%

Procedure

A solution of 4-[1-methyl-2,2,4-trioxo-6-(3-phenylprop-1-ynyl)-1,4-dihydro-2H-2λ6-benzo[1,2,6]-thiadiazin-3-ylmethyl]benzoic acid tert-butyl ester (0.075 g, 0.15 mmol) was treated with trifluoroacetic acid (5 mL), and the reaction mixture stirred at room temperature for 30 minutes. The solution was evaporated to dryness, the residue dissolved in ethyl acetate, washed with water, brine, and dried over MgSO4, and evaporated. Trituration with ethyl ether afforded a solid that was collected by filtration, washed with ethyl ether, and allowed to air dry under hose vacuum overnight. This afforded 0.015 g of 4-[1-methyl-2,2,4-trioxo-6-(3-phenylprop-1-ynyl)-1,4-dihydro-2H-2λ6-benzo[1,2,6]-thiadiazin-3-ylmethyl]benzoic acid as a light yellow solid (23.2% yield). 1H-NMR (CDCl3); d 8.24 (d, 1H), 8.08-8.05 (d, 2H), 7.69-7.66 (dd, 1H), 7.57-7.55 (d, 2H), 7.38-7.31 (m, 4H), 7.27-7.23 (m, 1H), 7.18-7.16 (d, 1H), 5.16 (s, 2H), 3.34 (s, 3H). MS: M++1=461.1 Da

Workup

  1. customThe solution was evaporated to dryness
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customTrituration with ethyl ether afforded a solid
  7. filtrationthat was collected by filtration
  8. washwashed with ethyl ether
  9. customto air dry under hose vacuum overnight

Sources & evidence

ORD record
ord-eee18fd6bbd747cdb872f29b801dc0f2
Source dataset
uspto-grants-2005_02
Patent number
US06849648B2

Reaction notes

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