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

HRID 7489

반응식

HRID 7489 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-dc1a01f5223a4d3995b814ec8f9224a4
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087602B2

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