1-Bromo-2-Chloroethane → HCID 59344699、化合物

HRID 18002

反応式

HRID 18002 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[F:27])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:12]([C:16](N(C)C)=[O:17])=[N:11][C:10]([OH:21])=[C:9]([OH:22])[C:8]=2[C:7]1=[O:23].C[O-:29].[Mg+2].C[O-].Br[CH2:34][CH2:35]Cl>CO.CS(C)=O.C(OCC)(=O)C.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[F:27])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:22])[C:10](=[O:21])[N:11]3[CH2:35][CH2:34][O:29][C:16](=[O:17])[C:12]3=2)[C:7]1=[O:23]

参加物

8

反応物 3

HCID 78491-Bromo-2-ChloroethaneHCID 164537Methanol, magnesium salt (2:1)HCID 178484497HCID 178484497、化合物

生成物 1

HCID 59344699HCID 59344699、化合物

試薬・触媒・溶媒 4

HCID 313Hydrochloric Acid溶媒HCID 679Dimethyl Sulfoxide溶媒2 回HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

A mixture of 6-(3-chloro-4-fluorobenzyl)-3,4-dihydroxy-N,N-dimethyl-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxamide (0.15 g, 0.39 μmmol; Example 1, Step 9) and magnesium methoxide in methanol (2 mL, 6-10% methanol solution available from Aldrich) in DMSO (4 mL) was heated at 60° C. for 30 minutes. Methanol was exhaustively removed under vacuum over 45 minutes. The resultant DMSO solution was treated with 1-bromo-2-chloroethane (0.28 g, 1.97 mmol) and stirred at 60° C. under an atmosphere of nitrogen overnight. The reaction mixture was diluted with ethyl acetate and dilute hydrochloric acid. The organic extract was washed with aqueous sodium sulfite, brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified by reverse phase high pressure liquid chromatography. Collection and lyophilization of appropriate fractions provided the title compound, which was recrystallized from a mixture of ethyl acetate and hexane

後処理

  1. customMethanol was exhaustively removed under vacuum over 45 minutes
  2. extractionThe organic extract
  3. washwas washed with aqueous sodium sulfite, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by reverse phase high pressure liquid chromatography
  8. customCollection and lyophilization of appropriate fractions

出典と根拠

ORDレコード
ord-bbf1e97e41e7415cb36be5abda3e68d2
出典データセット
uspto-grants-2010_06
特許番号
US07741315B2

関連ノート

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