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N2-Methyl-5-(trifluoromethyl)pyridine-2,3-diamine → 5-{4-(3-Methyl-6-trifluoromethylimidazo[5,4-b]pyridin-2-ylmethoxy)benzyl}thiazolidine-2,4-dione

HRID 1601775
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HRID 1601775 반응식
O=[CH:2][CH2:3][O:4][C:5]1[CH:18]=[CH:17][C:8]([CH2:9][CH:10]2[S:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])=[CH:7][CH:6]=1.[NH2:19][C:20]1[C:21]([NH:30][CH3:31])=[N:22][CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1>C(O)C.C(O)(=O)C>[CH3:31][N:30]1[C:21]2=[N:22][CH:23]=[C:24]([C:26]([F:29])([F:27])[F:28])[CH:25]=[C:20]2[N:19]=[C:2]1[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][CH:10]2[S:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])=[CH:17][CH:18]=1
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참가 물질

5

반응물 2

HCID 2735930N2-Methyl-5-(trifluoromethyl)pyridine-2,3-diamineHCID 108492775-[4-(2-Oxoethoxy)benzyl]thiazolidine-2,4-dione

생성물 1

HCID 106705615-{4-(3-Methyl-6-trifluoromethylimidazo[5,4-b]pyridin-2-ylmethoxy)benzyl}thiazolidine-2,4-dione수율 7.6%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 702Ethanol용매

실험 절차

4.16 g of 5-(4-(2-oxoethoxy)benzyl)thiazolidine-2,4-dione (prepared as described in Preparation 47) were added to a solution of 3.00 g of 3-amino-2-methylamino-5-trifluoromethylpyridine in a mixture of 6 ml of ethanol and 6 ml of acetic acid, and the resulting mixture was stirred at room temperature for 4 hours. At the end of this time, the reaction mixture was freed from the solvent by distillation under reduced pressure. 50 ml of 1,2-dimethoxyethane and 5.2 g of iodine were added to the residue, and the resulting mixture was stirred at 60° C. for one day. At the end of this time, the reaction mixture was poured into water, after which it was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, after which the solvent-was removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent. The product was crystallized by trituration with ethyl acetate, to give 520 mg of the title compound, melting at 212-214° C.

후처리

  1. distillationAt the end of this time, the reaction mixture was freed from the solvent by distillation under reduced pressure
  2. addition50 ml of 1,2-dimethoxyethane and 5.2 g of iodine were added to the residue
  3. stirringthe resulting mixture was stirred at 60° C. for one day
  4. additionAt the end of this time, the reaction mixture was poured into water
  5. extractionafter which it was extracted with ethyl acetate
  6. washThe extract was washed with an aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. customafter which the solvent-was removed by distillation under reduced pressure
  9. customThe residue was purified by column chromatography through silica gel
  10. additionby volume mixture of hexane and ethyl acetate as the eluent
  11. customThe product was crystallized by trituration with ethyl acetate

출처 및 근거

ORD 기록
ord-317860536eb94561ad8a79fb33cefb1b
출처 데이터셋
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05977365

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