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Dicyclohexylcarbodiimide → 3-[2-{2-(2-Oxopropyl)-1-cyclohexenyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine

HRID 276954
Notes
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Reaction equation

HRID 276954 reaction equation
[C:1]([CH2:4][C:5]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)=[O:2].[CH3:33]C1(C)OC(=O)CC(=O)O1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl.CN(C)C1C=CN=CC=1.C(O)(=O)C.O>[O:2]=[C:1]([CH3:33])[CH2:4][C:5]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:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[N:20][N:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=23)=[N:12]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 9910335FR-166124

Product 1

HCID 226292313-[2-{2-(2-Oxopropyl)-1-cyclohexenyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridineYield 25.1%

Reagents, catalysts & solvents 4

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 176Acetic AcidSolvent
HCID 962WaterSolvent
HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[2-(2-carboxymethyl-1-cyclohexenyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (2 g) in dichloromethane (20 ml) was added in turn 2,2-dimethyl-1,3-dioxane-4,6-dione (750 mg), 1,3-dicyclohexylcarbodiimide (1.1 g) and 4-dimethylaminopyridine (720 mg) at 0° C. A reaction mixture was allowed to warm to ambient temperature and stirred for overnight. Precipitate was removed by filtration, and mother liquor was washed with 1N-aqueous hydrochloric acid and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was dissolved in a mixture of acetic acid (15 ml) and water (15 ml), and which was. refluxed for 10 hours. A reaction mixture was extracted with ethyl acetate (200 ml) and organic layer was separated, which was neutralized with saturated sodium hydrogen carbonate in water. Organic phase was separated, washed in turn with 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 (100 g) eluting in turn with 33%, 50%, 80% ethyl acetate in n-hexane and ethyl acetate to give 3-[2-{2-(2-oxopropyl)-1-cyclohexenyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (0.5 g).

Workup

  1. customPrecipitate was removed by filtration, and mother liquor
  2. washwas washed with 1N-aqueous hydrochloric acid
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation of the solvent
  5. customgave a residue, which
  6. temperaturerefluxed for 10 hours
  7. extractionA reaction mixture was extracted with ethyl acetate (200 ml) and organic layer
  8. customwas separated
  9. customOrganic phase was separated
  10. washwashed in turn with saturated sodium hydrogen carbonate in water (50 ml) and brine (50 ml×2)
  11. dry with materialdried over magnesium sulfate
  12. customEvaporation of the solvent
  13. customgave a residue, which
  14. customwas chromatographed on silica gel (100 g)
  15. washeluting in turn with 33%, 50%, 80% ethyl acetate in n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-304421b865d64d068caeee7e4cea9c52
Source dataset
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06355640B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes