Sodium Bicarbonate → 3-oxa-6-azabicyclo[3.1.1]hept-6-yl(8-(1H-1,2,4-triazol-1-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl)methanone

HRID 931048노트

반응식

HRID 931048 반응식
[N:1]1([C:6]2[C:7]3[N:8]([C:16]([C:19]([OH:21])=O)=[CH:17][N:18]=3)[CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=2)[CH:5]=[N:4][CH:3]=[N:2]1.FC(F)(F)C(O)=O.[CH:29]12[CH2:35][CH:33]([NH:34]1)[CH2:32][O:31][CH2:30]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(N(CC)CC)C>[CH:33]12[CH2:35][CH:29]([N:34]1[C:19]([C:16]1[N:8]3[CH:9]=[C:10]([C:12]([F:14])([F:13])[F:15])[CH:11]=[C:6]([N:1]4[CH:5]=[N:4][CH:3]=[N:2]4)[C:7]3=[N:18][CH:17]=1)=[O:21])[CH2:30][O:31][CH2:32]2

참가 물질

7

반응물 4

HCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118378892HCID 118378892, 화합물HCID 118378980HCID 118378980, 화합물

생성물 1

HCID 1183789023-oxa-6-azabicyclo[3.1.1]hept-6-yl(8-(1H-1,2,4-triazol-1-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl)methanone수율 57.9%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

A mixture of 8-(1H-1,2,4-triazol-1-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylic acid (80 mg), 3-oxa-6-azabicyclo[3.1.1]heptane 2,2,2-trifluoroacetate (75 mg), HATU (133 mg), triethylamine (150 μL) and anhydrous DMF (3 mL) was stirred at room temperature for 12 hr, saturated aqueous sodium bicarbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane), and the obtained solid was recrystallized from ethyl acetate/hexane to give the title compound (59 mg).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  5. customthe obtained solid was recrystallized from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-26c40103094144b6bb5719446119ebfc
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296746B2

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