Trifluoroacetic acid → HCID 20755351, compound

HRID 22873Notes

Reaction equation

HRID 22873 reaction equation
C([O:5][C:6](=[O:36])[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:35])=[CH:9][CH:8]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:34][N:16]1[S:15](=[O:35])[N:14]([CH2:13][C:10]2[CH:9]=[CH:8][C:7]([C:6]([OH:36])=[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

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 207553754-[1-methyl-2,4-dioxo-6-(3-phenyl-prop-1-ynyl)-1,4-dihydro-2H-2lambda4-benzo[1,2,6]thiadiazin-3-ylmethyl]benzoic acid tert-butyl ester

Product 1

HCID 20755351HCID 20755351, compoundYield 10.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-[1-methyl-2,4-dioxo-6-(3-phenyl-prop-1-ynyl)-1,4-dihydro-2H-2λ4-benzo[1,2,6]thiadiazin-3-yl methyl]benzoic acid tert-butyl ester (0.33 g, 0.66 mmol) in methylene chloride (10 mL) was treated with trifluoroacetic acid (3 mL), and stirred at room temperature for 1 hour. The reaction mixture was evaporated to dryness, treated with hot ethyl acetate, allowed to cool, and the solid collected by filtration. The solid was triturated with ethyl ether, the solid collected by filtration, and allowed to air dry under house vacuum. The process afforded 0.03 g of 4-[1-methyl-2,4-dioxo-6-(3-phenyl-prop-1-ynyl)-1,4-dihydro-2H-2λ4-benzo[1,2,6]thiadiazin-3-yl methyl]benzoic acid as a blue/green solid (9.5% yield. 1H-NMR (CDCl3); d 8.30 (d, 1H), 8.08-8.06 (d, 2H), 7.69-7.67 (dd, 1H), 7.48-7.46 (d, 2H), 7.40-7.32 (m, 4H), 7.27-7.23 (m, 1H), 6.97-6.95 (d, 1H), 5.44-5.40 (d, 1H), 4.81-4.77 (d, 1H), 3.83 (s, 2H), 3.41 (s, 3H). MS: M++1=445.1 Da

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. additiontreated with hot ethyl acetate
  3. temperatureto cool
  4. filtrationthe solid collected by filtration
  5. customThe solid was triturated with ethyl ether
  6. filtrationthe solid collected by filtration
  7. customto air dry under house vacuum

Sources & evidence

ORD record
ord-0075f9bca7ac4c2599cdf584a89258f8
Source dataset
uspto-grants-2005_02
Patent number
US06849648B2

Reaction notes

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