Trifluoroacetic acid → HCID 66710870, 화합물

HRID 1895281노트

반응식

HRID 1895281 반응식
[N:1]1([C:10](=[N:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:11]2[C:16](=[O:17])[CH:15]=[CH:14][N:13]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[N:12]=2)C2C=CC=CC=2[N:3]=[N:2]1.[N-]=[N+]=[N-].[Na+].FC(F)(F)C(O)=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[C:29]1([N:28]2[C:10]([C:11]3[C:16](=[O:17])[CH:15]=[CH:14][N:13]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=4)[N:12]=3)=[N:1][N:2]=[N:3]2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

참가 물질

7

반응물 3

HCID 6422Trifluoroacetic acidHCID 33557Sodium AzideHCID 59436266HCID 59436266, 화합물

생성물 1

HCID 66710870HCID 66710870, 화합물수율 56%

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A solution of 3-[1H-benzotriazol-1-yl(phenylimino)methyl]-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one (0.094 g, 0.20 mmol), sodium azide (0.030 g, 0.46 mmol), and tetrabutylammonium bromide (0.015 g, 0.047 mmol) in methylene chloride (5 mL) and water (5 mL) was treated with trifluoroacetic acid (0.040 mL, 0.52 mmol) and stirred 24 h at room temperature. After that time, the organic layer was separated and the aqueous layer was extracted with methylene chloride (3×25 mL). The combined organic extracts were washed with saturated NaCl aqueous solution (50 mL), dried (MgSO4), and concentrated. The crude product purified by flash column chromatography (silica gel, 80:20 hexanes/ethyl acetate to ethyl acetate) to give an off-white solid that was recrystallized from ethyl acetate/hexanes to give 0.034 g (56%) of 3-(1-phenyl-1H-tetrazol-5-yl)-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one as colorless crystals.

후처리

  1. customAfter that time, the organic layer was separated
  2. extractionthe aqueous layer was extracted with methylene chloride (3×25 mL)
  3. washThe combined organic extracts were washed with saturated NaCl aqueous solution (50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product purified by flash column chromatography (silica gel, 80:20 hexanes/ethyl acetate to ethyl acetate)
  7. customto give an off-white solid
  8. customthat was recrystallized from ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-95974d99674e4bd3ab668912edb353e4
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513251B2

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