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

HRID 1360841노트

반응식

HRID 1360841 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6e9b9115d2074467a35e9578beb1780d
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879887B2

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