Triethylamine → 6-(3-Nitrophenyl)-7-pyridin-4-yl-pyrazolo[5,1-b]thiazole

HRID 38092ノート

反応式

HRID 38092 の反応式
O[CH:2]1[CH2:6][S:5][C:4]2=[C:7]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=3)=[N:9][N:3]12.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(N(CC)CC)C>C(COC)OC.C(OCC)(=O)C>[N+:16]([C:12]1[CH:11]=[C:10]([C:8]2[C:7]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)=[C:4]3[S:5][CH:6]=[CH:2][N:3]3[N:9]=2)[CH:15]=[CH:14][CH:13]=1)([O-:18])=[O:17]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 674426243-Hydroxy-6-(3-nitrophenyl)-7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazole

生成物 1

HCID 674230846-(3-Nitrophenyl)-7-pyridin-4-yl-pyrazolo[5,1-b]thiazole収率 44%

試薬・触媒・溶媒 2

HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

3-Hydroxy-6-(3-nitrophenyl)-7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazole (1 g, 2.938 mmol) was dissolved in dimethoxyethane (15 mL) under nitrogen atmosphere. Trifluoroacetic anhydride (0.8 mL, 5.664 mmol, 2 eq) and triethylamine (0.41 mL, 2.938 mmol, 1 eq) were added and the mixture was stirred at room temperature for 3 days. The solution was then diluted with ethyl acetate and washed with saturated aqueous NaHCO3 and brine, dried and evaporated to dryness. The crude product was purified by chromatography on silica gel (eluant: DCM/MeOH 97:3) to give 417 mg (44%) of 6-(3-nitrophenyl)-7-pyridin-4-yl-pyrazolo[5,1-b]thiazole as white solid.

後処理

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. customdried
  3. customevaporated to dryness
  4. customThe crude product was purified by chromatography on silica gel (eluant: DCM/MeOH 97:3)

出典と根拠

ORDレコード
ord-e1c0c9c50a1b408cb31653d5f47a20fb
出典データセット
uspto-grants-2013_09
特許番号
US08524707B2

反応ノート

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