Triethylamine → HCID 178513460, compound

HRID 1016600Notes

Reaction equation

HRID 1016600 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.[F:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1.C(N(CC)CC)C.[OH-].[Na+]>C(#N)C.CN(C1C=CN=CC=1)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][S:29]([C:26]3[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=3)(=[O:31])=[O:30])=[NH:20])[N:9]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 18407251HCID 18407251, compound

Product 1

HCID 178513460HCID 178513460, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Part B: To a stirred mixture of 3-(4-chlorophenyl)-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamidine (0.50 gram, 1.68 mmol) and 4-fluorophenylsulfonyl chloride (0.34 gram, 1.75 mmol) in acetonitrile (10 ml) was added N,N-dimethyl-4-aminopyridine (0.020 gram, 0.175 mmol) and triethylamine (1 ml). The resulting solution was stirred at room temperature for 30 minutes. After addition of a 2 N sodium hydroxide solution and extraction with ethylacetate (400 ml), the ethylacetate layer was concentrated in vacuo. The resulting crude residue was further purified by means of flash chromatography (petroleum ether/diethyl ether=1/1 (v/v), followed by ethylacetate). Subsequent concentration in vacuo afforded solid 3-(4-chlorophenyl)-4,5-dihydro-N-((4-fluorophenyl)sulfonyl)-4-phenyl-1H-pyrazole-1-carboxamidine (0.55 gram, 72% yield). Melting point: 214-215° C.

Workup

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

Sources & evidence

ORD record
ord-7d84f85483ba432fbe9d30f86eaf3f8f
Source dataset
uspto-grants-2002_11
Patent number
US06476060B2

Reaction notes

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