Ethylene Glycol → 2-bromo-2-methyl-N-(4-trifluoromethyl-6H-pyrazolo[4',3':3,4]benzo[1,2-d]thiazol-2-yl)-propionamide

HRID 1360841Notes

Reaction equation

HRID 1360841 reaction equation
[Br:1][C:2]([CH3:29])([CH3:28])[C:3]([NH:5][C:6]1[S:7][C:8]2[C:14]3[CH:15]=[N:16][N:17](C(=O)C(Br)(C)C)[C:13]=3[CH:12]=[C:11]([C:24]([F:27])([F:26])[F:25])[C:9]=2[N:10]=1)=[O:4].O1CCCC1.C(O)CO.C(N(CC)CC)C>C(OCC)(=O)C.O>[Br:1][C:2]([CH3:29])([CH3:28])[C:3]([NH:5][C:6]1[S:7][C:8]2[C:14]3[CH:15]=[N:16][NH:17][C:13]=3[CH:12]=[C:11]([C:24]([F:25])([F:26])[F:27])[C:9]=2[N:10]=1)=[O:4]

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 579512872-bromo-N-[6-(2-bromo-2-methyl-propionyl)-4-trifluoromethyl-6H-pyrazolo[4',3':3,4]benzo[1,2-d]thiazol-2-yl]-2-methyl-propionamide

Product 1

HCID 579513762-bromo-2-methyl-N-(4-trifluoromethyl-6H-pyrazolo[4',3':3,4]benzo[1,2-d]thiazol-2-yl)-propionamideYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4.32 g of 2-bromo-N-[6-(2-bromo-2-methyl-propionyl)-4-trifluoromethyl-6H-pyrazolo[4′,3′:3,4]benzo[1,2-d]thiazol-2-yl]-2-methyl-propionamide, 25 ml of tetrahydrofuran, 10 ml of ethyleneglycol and 1.30 ml of triethylamine was stirred at room temperature for 14 hours. After the completion of the reaction was confirmed by HPLC, water and ethyl acetate were added and then portioned. The ethyl acetate layer was washed with 1M hydrochoric acid, water and brine and dried over magnesium sulfate, filtered, and then concentrated to dryness under reduced pressure. Hexane was added to the residue and the solid was collected by filtration to give 2.87 g (yield: 91%) of 2-bromo-2-methyl-N-(4-trifluoromethyl-6H-pyrazolo[4′,3′:3,4]benzo[1,2-d]thiazol-2-yl)-propionamide as a pale yellow solid.

Workup

  1. additionwere added
  2. washThe ethyl acetate layer was washed with 1M hydrochoric acid, water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. additionHexane was added to the residue
  7. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-6e9b9115d2074467a35e9578beb1780d
Source dataset
uspto-grants-2011_02
Patent number
US07879887B2

Reaction notes

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