Hydrochloric Acid → 4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-amine

HRID 1727356ノート

反応式

HRID 1727356 の反応式
C(OC([NH:8][C:9]1[CH:14]=[C:13]([C:15]2[S:19][C:18]([CH2:20][CH3:21])=[N:17][C:16]=2[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[CH:23]=2)[CH:12]=[CH:11][N:10]=1)=O)(C)(C)C.C(OC(NC1C=C(CC(C2C=CC=C(C)C=2)=O)C=CN=1)=O)(C)(C)C.Cl>C(=O)([O-])O.[Na+]>[CH2:20]([C:18]1[S:19][C:15]([C:13]2[CH:12]=[CH:11][N:10]=[C:9]([NH2:8])[CH:14]=2)=[C:16]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[CH:23]=2)[N:17]=1)[CH3:21]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 102720365-[2-(Tert-butoxycarbonylamino)-4-pyridyl]-2-ethyl-4-(3-methylphenyl)-1,3-thiazoleHCID 116168302-(2-Tert-butoxycarbonylamino-4-pyridyl)-1-(3-methylphenyl)ethanone

生成物 1

HCID 98573494-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-amine収率 55%

試薬・触媒・溶媒 1

HCID 516892Sodium Bicarbonate溶媒2 回

反応条件

温度
100 °C

実験手順

To 5-[2-(tert-butoxycarbonylamino)-4-pyridyl]-2-ethyl-4-(3-methylphenyl)-1,3-thiazole (synthesized from 2-(2-tert-butoxycarbonylamino-4-pyridyl)-1-(3-methylphenyl)ethanone (35 g, 170 mmol) according to the method described in Example 3) was added 2N-hydrochloric acid (200 mL), and the mixture was stirred for 1 hour at 100° C. The reaction mixture was cooled to room temperature, then, made alkaline with a 2N aqueous sodium hydrogen carbonate solution (200 mL) and aqueous sodium hydrogen carbonate solution. The resulted mixture was extracted by ethyl acetate, and the extracts were washed with water. This extracts were dried and concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=1:1) to obtain a crystal. This crystal was washed with isopropyl ether, to obtain a title compound (17 g, yield 55%).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe resulted mixture was extracted by ethyl acetate
  3. washthe extracts were washed with water
  4. customThis extracts were dried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate=1:1)
  7. customto obtain a crystal
  8. washThis crystal was washed with isopropyl ether

出典と根拠

ORDレコード
ord-4769c473166842dcb6e84b204d7b1823
出典データセット
uspto-grants-2009_02
特許番号
US07495018B2

反応ノート

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