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Dichloromethane → 4-Phenyl-1-{[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-7-yl]methyl}pyrrolidin-2-one

HRID 1896465
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HRID 1896465 반응식
Cl.[NH2:2][CH2:3][CH:4]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:5][C:6]([O:8]C)=O.[F:16][C:17]([F:30])([F:29])[C:18]1[N:22]2[N:23]=[CH:24][C:25]([CH:27]=O)=[CH:26][C:21]2=[N:20][N:19]=1.C(N(CC)CC)C.ClCCl>ClC(Cl)C.COCCOC>[C:10]1([CH:4]2[CH2:3][N:2]([CH2:27][C:25]3[CH:24]=[N:23][N:22]4[C:18]([C:17]([F:30])([F:16])[F:29])=[N:19][N:20]=[C:21]4[CH:26]=3)[C:6](=[O:8])[CH2:5]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1
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참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 536292043-(Trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine-7-carbaldehydeHCID 68748102Methyl 4-amino-3-phenylbutanoate hydrochloride

생성물 1

HCID 577430604-Phenyl-1-{[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-7-yl]methyl}pyrrolidin-2-one수율 36%

시약·촉매·용매 2

HCID 63651,1-Dichloroethane용매
HCID 80711,2-Dimethoxyethane용매

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온도
11 °C

실험 절차

Methyl 4-amino-3-phenylbutanoate hydrochloride x11 (0.19 g, 0.83 mmol, 1.05 eq) is added to a solution of aldehyde x235 (0.17 g, 0.79 mmol) in dry dichloroethane (DCE) (7.8 ml). The mixture is kept at room temperature for 30 min, cooled to 10-12° C., and a solution of triethylamine (0.15 ml, 0.83 mmol, 1.05 eq) in dry DME (2.5 ml) is added dropwise. The mixture is additionally stirred at the same temperature for 1 h and cooled to 0-5° C. Then STAB (0.23 g, 1.10 mmol, 1.4 eq) is added in portions under vigorous stirring. The mixture is additionally stirred at 0-5° C. for 30 min and kept at room temperature overnight. Then the mixture is heated to 60° C. for 2 h and cooled to room temperature. An equal volume of dichloromethane is added, and the mixture is washed with 10% K2CO3 (2×10 ml). The mixture is dried over anhydrous Na2SO4 and evaporated. The oily residue is triturated with ether, and the formed crystals are separated by filtration, washed twice with ether, and vacuum-dried to give white fine-crystalline 4-phenyl-1-{[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-7-yl]methyl}pyrrolidin-2-one 255.

후처리

  1. temperaturecooled to 0-5° C
  2. additionThen STAB (0.23 g, 1.10 mmol, 1.4 eq) is added in portions under vigorous stirring
  3. stirringThe mixture is additionally stirred at 0-5° C. for 30 min
  4. waitkept at room temperature overnight
  5. temperatureThen the mixture is heated to 60° C. for 2 h
  6. temperaturecooled to room temperature
  7. washthe mixture is washed with 10% K2CO3 (2×10 ml)
  8. dry with materialThe mixture is dried over anhydrous Na2SO4
  9. customevaporated
  10. customThe oily residue is triturated with ether
  11. customthe formed crystals are separated by filtration
  12. washwashed twice with ether
  13. customvacuum-dried

출처 및 근거

ORD 기록
ord-5a30c4d1ceaa4b2b9d1e4793f690e873
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08518943B2

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