Triethylamine → HCID 141040557, compound

HRID 1016601Notes

Reaction equation

HRID 1016601 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][N:10]([C:19]([NH2:21])=[NH:20])[N:9]=2)=[CH:4][CH:3]=1.[C:22]1([C:32](Cl)=[O:33])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C.[OH-].[Na+]>C(#N)C.C(OC(=O)C)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][N:10]([C:19]([NH:21][C:32]([C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:25]=[CH:24][CH:23]=3)=[O:33])=[NH:20])[N:9]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 701461-Naphthalenecarbonyl chlorideHCID 18407251HCID 18407251, compound

Product 1

HCID 141040557HCID 141040557, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of 3-(4-chlorophenyl)-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamidine (0.75 gram, 2.50 mmol) and 1-naphtoyl chloride (0.4 ml, 2.70 mmol) in acetonitrile (15 ml) was added triethylamine (1 ml). The resulting mixture was stirred at room temperature for 1 hour. After addition of a 2 N sodium hydroxide solution and extraction with ethylacetate, the ethylacetate layer was concentrated in vacua. The resulting crude residue was further purified by means of flash chromatography (petroleum ether/diethyl ether=3/1 (v/v), followed by ethylacetate). Subsequent concentration in vacuo afforded 3-(4-chlorophenyl)-4,5-dihydro-N-(1-naphtoyl)-4-phenyl-1H-pyrazole-1-carboxamidine (0.94 gram, 83% yield). Melting point: 206-207° C.

Workup

  1. concentrationthe ethylacetate layer was concentrated in vacua
  2. customThe resulting crude residue was further purified by means of flash chromatography (petroleum ether/diethyl ether=3/1 (v/v), followed by ethylacetate)
  3. concentrationSubsequent concentration in vacuo

Sources & evidence

ORD record
ord-b8fdb221beab439b985e7355eb449c3b
Source dataset
uspto-grants-2002_11
Patent number
US06476060B2

Reaction notes

Loading…