Ammonium Chloride → 3-(7-Pyridin-4-yl-pyrazolo[5,1-b]thiazol-6-yl)-phenylamine

HRID 38093ノート

反応式

HRID 38093 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:17]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[C:13]3[S:14][CH:15]=[CH:16][N:12]3[N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.[Cl-].[NH4+].C([O-])(O)=O.[Na+]>O1CCOCC1.O.O.[Zn]>[N:21]1[CH:20]=[CH:19][C:18]([C:17]2[C:10]([C:6]3[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][CH:7]=3)=[N:11][N:12]3[CH:16]=[CH:15][S:14][C:13]=23)=[CH:23][CH:22]=1

参加物

7

反応物 3

HCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 674230846-(3-Nitrophenyl)-7-pyridin-4-yl-pyrazolo[5,1-b]thiazole

生成物 1

HCID 674239983-(7-Pyridin-4-yl-pyrazolo[5,1-b]thiazol-6-yl)-phenylamine収率 68.6%

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 962Water溶媒HCID 218864351,4-Dioxane--water (1/1)溶媒

反応条件

温度
100 °C

実験手順

6-(3-Nitrophenyl)-7-pyridin-4-yl-pyrazolo[5,1-b]thiazole (410 mg, 1.272 mmol) was dissolved in a 3:1 dioxane/water mixture (8 mL). Zinc powder (333 mg, 5.094 mmol, 4 eq) and ammonium chloride (680 mg, 12.72 mmol, 10 eq) were added and the mixture was stirred at 100° C. for 2 hours. It was then diluted with water, made basic by addition of saturated aqueous NaHCO3 and extracted with ethyl acetate (3×20 mL). Combined organic layers were washed with sat. aq. NaHCO3 and brine, dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (DCM/MeOH 97:3) to give 255 mg (68%) of 3-(7-pyridin-4-yl-pyrazolo[5,1-b]thiazol-6-yl)-phenylamine as white solid.

後処理

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. washCombined organic layers were washed with sat. aq. NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by chromatography on silica gel (DCM/MeOH 97:3)

出典と根拠

ORDレコード
ord-d67425bcdd5e47818c01ea2b655a50cc
出典データセット
uspto-grants-2013_09
特許番号
US08524707B2

反応ノート

読み込み中…