Acetyl chloride → N-[6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-isobutyl-3-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]acetamide

HRID 13825ノート

反応式

HRID 13825 の反応式
[NH2:1][C:2]1[C:11]2[C:6](=[N:7][C:8]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[Cl:26])=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[CH:10]=2)[N:5]([CH2:27][CH:28]([CH3:30])[CH3:29])[C:4](=[O:31])[C:3]=1[CH3:32].[H-].[Na+].[C:35](Cl)(=[O:37])[CH3:36]>C1COCC1.CCOC(C)=O>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([C:9]2[CH:10]=[C:11]3[C:6](=[N:7][C:8]=2[C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[Cl:26])[N:5]([CH2:27][CH:28]([CH3:29])[CH3:30])[C:4](=[O:31])[C:3]([CH3:32])=[C:2]3[NH:1][C:35](=[O:37])[CH3:36])=[CH:17][CH:16]=1

参加物

6

反応物 3

HCID 6367Acetyl chloride2 回HCID 24758Sodium hydrideHCID 113751874-amino-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-isobutyl-3-methyl-1,8-naphthyridin-2(1H)-one

生成物 1

HCID 11466703N-[6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-isobutyl-3-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]acetamide

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To the product of EXAMPLE 42 (28 mg) in THF (0.5 mL) at 0° C. was added NaH (5 mg, 60% dispersion in mineral oil). The reaction stirred 10 minutes before acetyl chloride (7 μL) was added. Two hours later an additional 20 μL portion of acetyl chloride was added and again after an additional 90 minutes. After an additional hour of reaction time the reaction was diluted with EtOAc and washed with saturated aqueous NaHCO3 solution and dried (Na2SO4). The concentrated residue was purified by preparative TLC on silica gel eluted with 70% EtOAc in hexane affording the title compound. HPLC/MS: 528.0 (M+1), 530.0 (M+3); Rt=4.27 min.

後処理

  1. additionwas added
  2. customAfter an additional hour of reaction time the reaction
  3. washwashed with saturated aqueous NaHCO3 solution
  4. dry with materialdried (Na2SO4)
  5. customThe concentrated residue was purified by preparative TLC on silica gel
  6. washeluted with 70% EtOAc in hexane affording the title compound

出典と根拠

ORDレコード
ord-a2bbbca5b4704590b956ca2167a03084
出典データセット
uspto-grants-2010_06
特許番号
US07728141B2

反応ノート

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