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Triethylamine → 1-[3-(2-Phenylpyrazolo[1,5-a]pyridin-3-yl)acryloyl]-2-ethylpiperidine

HRID 487615
Notes
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Reaction equation

HRID 487615 reaction equation
ClC(OCC(C)C)=O.[C:9]1([C:15]2[C:23]([CH:24]=[CH:25][C:26](O)=[O:27])=[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][N:17]3[N:16]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C.[CH2:36]([CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][NH:39]1)[CH3:37]>C(Cl)Cl.O1CCCC1>[C:9]1([C:15]2[C:23]([CH:24]=[CH:25][C:26]([N:39]3[CH2:40][CH2:41][CH2:42][CH2:43][CH:38]3[CH2:36][CH3:37])=[O:27])=[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][N:17]3[N:16]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 942052-EthylpiperidineHCID 53923255HCID 53923255, compound

Product 1

HCID 540385431-[3-(2-Phenylpyrazolo[1,5-a]pyridin-3-yl)acryloyl]-2-ethylpiperidineYield 47.8%

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
HCID 8028TetrahydrofuranSolvent2×

Procedure

Isobutyl chloroformate (1.04 g) was added dropwise to a mixture of 3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acrylic acid (trans isomer) (2.0 g) and triethylamine (0.766 g) in methylene chloride (40 ml) and tetrahydrofuran (10 ml) at -20° C. with stirring. After being stirred at the same temperature for 30 minutes, a solution of 2-ethylpiperidine (0.942 g) in tetrahydrofuran (10 ml) was added thereto dropwise at -20° C. and the mixture was stirred at -20° C. to 10° C. for 2 hours. The mixture was warmed to room temperature and evaporated in vacuo. A saturated sodium bicarbonate solution was added to the residue and extracted twice with chloroform (50 ml), dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (40 g) with chloroform as an eluent. The fractions containing the object compound were combined and evaporated in vacuo to give 1-[3-(2-phenylpyrazolo[1,5 -a]pyridin-3-yl)acryloyl]-2-ethylpiperidine (trans isomer) (1.30 g) as an oil.

Workup

  1. stirringAfter being stirred at the same temperature for 30 minutes
  2. stirringdropwise at -20° C. and the mixture was stirred at -20° C. to 10° C. for 2 hours
  3. customevaporated in vacuo
  4. additionA saturated sodium bicarbonate solution was added to the residue
  5. extractionextracted twice with chloroform (50 ml)
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was chromatographed on silica gel (40 g) with chloroform as an eluent
  9. additionThe fractions containing the object compound
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-bf89d8a8629a4bcab8e9edc41d4d3c7c
Source dataset
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05296490

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes