Dichloromethane → 3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-[(3-methylcarbamoyl-propoxyamino)-methyl]-benzamide

HRID 2038625ノート

反応式

HRID 2038625 の反応式
[F:1][C:2]1[C:3]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([I:33])=[CH:29][C:28]=2[F:34])=[C:4]([CH:12]=[C:13](/[CH:16]=[N:17]/[O:18][CH2:19][CH2:20][CH2:21][C:22](=[O:25])[NH:23][CH3:24])[C:14]=1[F:15])[C:5]([NH:7][O:8][CH2:9][CH2:10][OH:11])=[O:6].ClCCl.ClC(Cl)C(O)=O>C(OCC)(=O)C>[F:1][C:2]1[C:3]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([I:33])=[CH:29][C:28]=2[F:34])=[C:4]([CH:12]=[C:13]([CH2:16][NH:17][O:18][CH2:19][CH2:20][CH2:21][C:22](=[O:25])[NH:23][CH3:24])[C:14]=1[F:15])[C:5]([NH:7][O:8][CH2:9][CH2:10][OH:11])=[O:6]

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 6597Dichloroacetic AcidHCID 231323693,4-difluoro-2-(2-fluoro-4-iodoanilino)-N-(2-hydroxyethoxy)-5-[(E)-[4-(methylamino)-4-oxobutoxy]iminomethyl]benzamide

生成物 1

HCID 115924153,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-[(3-methylcarbamoyl-propoxyamino)-methyl]-benzamide収率 65%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To (E)-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-[(3-methylcarbamoyl-propoxyimino)-methyl]-benzamide (50 mg, 0.084 mmol) obtained in Step C was added dichloromethane (6 ml). The mixture was stirred at room temperature, and borane-pyridine complex (67 μl, 0.673 mmol) and dichloroacetic acid (55 μl, 0.673 mmol) were added thereto. After stirring for 14 hours, the reaction mixture was diluted with ethyl acetate, and washed with purified water and saturated aqueous sodium chloride. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-[(3-methylcarbamoyl-propoxyamino)-methyl]-benzamide (Compound C-21, 32 mg, 65% yield).

後処理

  1. stirringAfter stirring for 14 hours
  2. washwashed with purified water and saturated aqueous sodium chloride
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-f9c3a402f0344070aa44869a957daf6c
出典データセット
uspto-grants-2013_11
特許番号
US08575391B2

反応ノート

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