Ethyl Acetate → Ethyl 6-[7-ethyl-4-(4-fluorophenyl)-2-methylpyrrolo[1,2-b]pyridazin-3-yl]hexanoate

HRID 860440ノート

反応式

HRID 860440 の反応式
[F:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([CH:8]([C:19](=O)[CH3:20])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=O)=[CH:4][CH:3]=1.[NH2:24][N:25]1[C:29]([CH2:30][CH3:31])=[CH:28][CH:27]=[C:26]1[C:32]([C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1)=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>C(O)C.O>[CH2:30]([C:29]1[N:25]2[N:24]=[C:6]([C:5]3[CH:22]=[CH:23][C:2]([F:1])=[CH:3][CH:4]=3)[C:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:32]([C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=3)[C:26]2=[CH:27][CH:28]=1)[CH3:31].[CH2:32]([C:26]1[N:25]2[N:24]=[C:19]([CH3:20])[C:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:6]([C:5]3[CH:22]=[CH:23][C:2]([F:1])=[CH:3][CH:4]=3)[C:29]2=[CH:28][CH:27]=1)[CH3:34]

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 521998p-Toluenesulfonic acid monohydrateHCID 57444527Ethyl 7-(4-fluorobenzoyl)-8-oxononanoateHCID 69311541(1-amino-5-ethyl-1H-pyrrol-2-yl)(4-fluorophenyl)methanone

生成物 2

HCID 69308101Ethyl 6-[7-ethyl-4-(4-fluorophenyl)-2-methylpyrrolo[1,2-b]pyridazin-3-yl]hexanoateHCID 69308766Ethyl 6-[7-ethyl-2,4-bis(4-fluorophenyl)pyrrolo[1,2-b]pyridazin-3-yl]hexanoate

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

A mixture of ethyl 7-(4-fluorobenzoyl)-8-oxononanoate (300 mg), (1-amino-5-ethyl-1H-pyrrol-2-yl)(4-fluorophenyl)methanone (216 mg), and p-toluenesulfonic acid monohydrate (35.4 mg) in ethanol (6 ml) was refluxed for 5 hours. The mixture was partioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:4) to give ethyl 6-[7-ethyl-2,4-bis(4-fluorophenyl)pyrrolo[1,2-b]pyridazin-3-yl]hexanoate (83 mg) and ethyl 6-[7-ethyl-4-(4-fluorophenyl)-2-methylpyrrolo[1,2-b]pyridazin-3-yl]hexanoate (40 mg) as an oil.

後処理

  1. temperaturewas refluxed for 5 hours
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:4)

出典と根拠

ORDレコード
ord-a936da50096a4a398d4d232617be9aa1
出典データセット
uspto-grants-2006_12
特許番号
US07153854B2

反応ノート

読み込み中…