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

Reaction equation

HRID 276947 reaction equation
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]

Participants

8

Reactant 4

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

Product 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

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-934bdefab5484275b4460cda51fde13e
Source dataset
uspto-grants-2002_03
Patent number
US06355640B1

Linked notes

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