Hydrochloric Acid → 4-Chloro-6-methoxy-7-[(2-methylthiazol-4-yl)methoxy]cinnoline

HRID 1057342ノート

反応式

HRID 1057342 の反応式
C(=O)([O-])[O-].[K+].[K+].Cl[CH2:8][C:9]1[N:10]=[C:11]([CH3:14])[S:12][CH:13]=1.[Cl:15][C:16]1[C:25]2[C:20](=[CH:21][C:22]([OH:28])=[C:23]([O:26][CH3:27])[CH:24]=2)[N:19]=[N:18][CH:17]=1.Cl>CN(C=O)C.O>[Cl:15][C:16]1[C:25]2[C:20](=[CH:21][C:22]([O:28][CH2:8][C:9]3[N:10]=[C:11]([CH3:14])[S:12][CH:13]=3)=[C:23]([O:26][CH3:27])[CH:24]=2)[N:19]=[N:18][CH:17]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 7363414-(Chloromethyl)-2-methyl-1,3-thiazoleHCID 1357525234-Chloro-7-hydroxy-6-methoxycinnoline

生成物 1

HCID 219910614-Chloro-6-methoxy-7-[(2-methylthiazol-4-yl)methoxy]cinnoline収率 48%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

The starting material 4-chloro-6-methoxy-7-[(2-methylthiazol-4-yl)methoxy]cinnoline was obtained by adding potassium carbonate (786 mg, 5.7 mmol) followed by 4-chloromethyl-2-methylthiazole (308 mg, 2 mmol) to a suspension of 4-chloro-7-hydroxy-6-methoxycinnoline (0.4 g, 1.9 mmol), (prepared as described for the starting material in Example 10), in DMF (10 ml). After stirring for 4.5 hours at 60° C., the reaction mixture was diluted with water and acidified to pH4 with 2M hydrochloric acid. After extraction with ethyl acetate, the organic layer was washed with water and then brine, dried (MgSO4) and the solvent evaporated. The residue was purified by flash chromatography using methylene chloride/ethyl acetate (2/8) as eluent to give 4-chloro-6-methoxy-7-[(2-methylthiazol-4-yl)methoxy]cinnoline as a solid (293 mg, 48%).

後処理

  1. custom(prepared
  2. extractionAfter extraction with ethyl acetate
  3. washthe organic layer was washed with water
  4. dry with materialbrine, dried (MgSO4)
  5. customthe solvent evaporated
  6. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-daa644418a7d48f0895674d6aebbffcc
出典データセット
uspto-grants-2003_02
特許番号
US06514971B1

反応ノート

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