Hydrochloric Acid → 5-Acetyl-4-[(3,5-dichloropyridin-4-yl)amino]-2-ethyl-6-phenylpyridazin-3(2H)-one

HRID 1725520

反応式

HRID 1725520 の反応式
[H-].[Na+].[NH2:3][C:4]1[C:9]([Cl:10])=[CH:8][N:7]=[CH:6][C:5]=1[Cl:11].[C:12]([C:15]1[C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:19][N:18]([CH2:27][CH3:28])[C:17](=[O:29])[C:16]=1[N+]([O-])=O)(=[O:14])[CH3:13].Cl>C1COCC1.C(OCC)(=O)C>[C:12]([C:15]1[C:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[N:19][N:18]([CH2:27][CH3:28])[C:17](=[O:29])[C:16]=1[NH:3][C:4]1[C:9]([Cl:10])=[CH:8][N:7]=[CH:6][C:5]=1[Cl:11])(=[O:14])[CH3:13]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 898884-Amino-3,5-dichloropyridineHCID 107320155-acetyl-2-ethylnitro6-phenylpyridazin-3(2H)-one

生成物 1

HCID 671092825-Acetyl-4-[(3,5-dichloropyridin-4-yl)amino]-2-ethyl-6-phenylpyridazin-3(2H)-one収率 16.7%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒3 回HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred suspension of 50 mg (1.25 mmol) of sodium hydride in 5 ml of THF, 100 mg (0.62 mmol) of 4-amino-3,5-dichloropyridine in 5 ml of THF was added. The mixture was allowed stirring 30 minutes at room temperature and then cooled to 0° C. 150 mg (0.52 mmol) of 5-acetyl-2-ethyl-4-nitro-6-phenylpyridazin-3(2H)-one (Dal Piaz, V et al, J. Med. Chem. 1997, 40, 1417) in 10 ml of THF was added. The reaction was allowed to warm to room temperature and to continue stirring for 12 hours. The mixture was acidified with 2N HCl to pH 2. Ethyl acetate was added and the organic layer was washed with water, brine, dried over Na2SO4 anhydride and evaporated. The residue obtained (210 mg) was purified by column chromatography (silica gel, hexane/ethyl acetate 1:1) to yield the title compound (35 mg, 16.7% yield).

後処理

  1. additionwas added
  2. temperaturecooled to 0° C
  3. temperatureto warm to room temperature
  4. stirringto continue stirring for 12 hours
  5. washthe organic layer was washed with water, brine
  6. dry with materialdried over Na2SO4 anhydride
  7. customevaporated
  8. customThe residue obtained (210 mg)
  9. customwas purified by column chromatography (silica gel, hexane/ethyl acetate 1:1)

出典と根拠

ORDレコード
ord-193fcd27e4d24c10aacff4977b15babe
出典データセット
uspto-grants-2009_02
特許番号
US07491722B2

関連ノート

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