1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-[2-{2-(N-ethoxycarbonylmethyl-N-methylcarbamoyl)methyl-1-cyclohexenyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine

HRID 276947

反応式

HRID 276947 の反応式
C(CC1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=1[N:11]1[C:16](=[O:17])[CH:15]=[CH:14][C:13]([C:18]2[C:19]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:20][N:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=23)=[N:12]1)(O)=O.[OH:33]N1C2C=CC=CC=2N=N1.C(N=C=N[CH2:48][CH2:49][CH2:50][N:51]([CH3:53])[CH3:52])C.Cl.[CH2:55]([O:57][C:58](=[O:62])CNC)[CH3:56]>O1CCCC1.ClCCl.C(OCC)(=O)C>[CH2:55]([O:57][C:58]([CH2:53][N:51]([CH3:52])[C:50]([CH2:49][C:48]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=1[N:11]1[C:16](=[O:17])[CH:15]=[CH:14][C:13]([C:18]2[C:19]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:20][N:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=23)=[N:12]1)=[O:33])=[O:62])[CH3:56]

参加物

8

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 9910335FR-166124

生成物 1

HCID 226292113-[2-{2-(N-ethoxycarbonylmethyl-N-methylcarbamoyl)methyl-1-cyclohexenyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 3-[2-(2-carboxymethyl-1-cyclohexenyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (1.5 g) in a mixture of tetrahydrofuran (20 ml) and dichloromethane (20 ml) was added in turn with 1-hydroxybenzotriazole (563 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (950 μl) and sarcosine ethyl ester hydrochloride (640 mg) at room temperature. The reaction mixture was stirred for two hours, which was poured into ethyl acetate (300 ml), washed in turn with water (30 ml×2), saturated sodium hydrogen carbonate in water (50 ml) and brine (50 ml×2), and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (200 ml) eluting with ethyl acetate. Fractions containing desired product were collected. Evaporation of the solvent gave a residue, which was recrystallized from a mixture of ethyl acetate and n-hexane to give 3-[2-{2-(N-ethoxycarbonylmethyl-N-methylcarbamoyl)methyl-1-cyclohexenyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (1.12 g).

後処理

  1. washwashed in turn with water (30 ml×2), saturated sodium hydrogen carbonate in water (50 ml) and brine (50 ml×2)
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation of the solvent
  4. customgave a residue, which
  5. customwas chromatographed on silica gel (200 ml)
  6. washeluting with ethyl acetate
  7. additionFractions containing desired product
  8. customwere collected
  9. customEvaporation of the solvent
  10. customgave a residue, which
  11. customwas recrystallized from a mixture of ethyl acetate and n-hexane

出典と根拠

ORDレコード
ord-934bdefab5484275b4460cda51fde13e
出典データセット
uspto-grants-2002_03
特許番号
US06355640B1

関連ノート

読み込み中…