Hydrochloric Acid → 4-(4-(2-(4-(3-Trifluoromethylphenyl)piperazinyl)ethyl)phenyl)-2-amino-5-methylthiazole

HRID 329396

反応式

HRID 329396 の反応式
Br.Cl[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([NH2:16])[S:14][CH:15]=2)=[CH:7][CH:6]=1.Cl.[F:18][C:19]([F:33])([F:32])[C:20]1[CH:21]=[C:22]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:23]=[CH:24][CH:25]=1.[CH2:34](N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].Cl>C(OCC)(=O)C.O.C(OCC)(=O)C.CO.CCOCC.C(O)C>[F:33][C:19]([F:18])([F:32])[C:20]1[CH:21]=[C:22]([N:26]2[CH2:31][CH2:30][N:29]([CH2:3][CH2:4][C:5]3[CH:10]=[CH:9][C:8]([C:11]4[N:12]=[C:13]([NH2:16])[S:14][C:15]=4[CH3:34])=[CH:7][CH:6]=3)[CH2:28][CH2:27]2)[CH:23]=[CH:24][CH:25]=1

参加物

11

反応物 6

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 3084246TFMPP hydrochlorideHCID 147269834-(2-Chloroethyl)phenyl-2-aminothiazole hydrobromide

生成物 1

HCID 147269984-(4-(2-(4-(3-Trifluoromethylphenyl)piperazinyl)ethyl)phenyl)-2-amino-5-methylthiazole

試薬・触媒・溶媒 4

HCID 702Ethanol溶媒HCID 3283Diethyl Ether溶媒HCID 21584119Ethylacetate methanol溶媒HCID 22728543Water ethylacetate溶媒

実験手順

To a 35 ml round-bottomed flask equipped with condenser and N2 inlet were added 0.75 g (2.59 mmol) of 4-(4-(2-chloroethyl)phenyl)-2-aminothiazole hydrobromide, 0.69 g (2.59 mmol) of N-(3-trifluoromethylphenyl)piperazine hydrochloride, 1.08 ml (7.78 mmol) of triethylamine, 0.27 g (2.59 mmol) of sodium carbonate, 5 mg of sodium iodide, and 9.5 ml of ethanol. The reaction was heated at reflux, cooled, and taken up in ethyl acetate/water. The layers were separated, the ethyl acetate washed with brine, dried, and evaporated to give an oil. The oil was chromatographed on silica gel using ethyl acetate as eluent to give an oil. The oil was taken up in ethyl acetate/methanol, ether saturated with HCl was added, the precipitate filtered, washed with ether, and dried to give a white solid, 0.72 g (50%), m.p. 110°-115° C.

後処理

  1. customTo a 35 ml round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was heated
  3. temperatureat reflux
  4. temperaturecooled
  5. customThe layers were separated
  6. washthe ethyl acetate washed with brine
  7. customdried
  8. customevaporated
  9. customto give an oil
  10. customThe oil was chromatographed on silica gel
  11. customto give an oil
  12. filtrationthe precipitate filtered
  13. washwashed with ether
  14. customdried
  15. customto give a white solid, 0.72 g (50%), m.p. 110°-115° C.

出典と根拠

ORDレコード
ord-496521a9e8c74e6dad62f6677c2deacd
出典データセット
uspto-grants-1990_01
特許番号
US04891375

関連ノート

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