1-(4-Fluorophenyl)piperazine → (5-Amino-3-(2-fluorophenyl)isoxazol-4-yl)(4-(4-fluorophenyl)piperazine-1-yl)methanone

HRID 2276482Notes

Reaction equation

HRID 2276482 reaction equation
[NH2:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[F:13])[C:3]=1[C:14]([OH:16])=O.Cl.C(N=C=NCCCN(C)C)C.[F:29][C:30]1[CH:35]=[CH:34][C:33]([N:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)=[CH:32][CH:31]=1>ClCCl>[NH2:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[F:13])[C:3]=1[C:14]([N:39]1[CH2:38][CH2:37][N:36]([C:33]2[CH:32]=[CH:31][C:30]([F:29])=[CH:35][CH:34]=2)[CH2:41][CH2:40]1)=[O:16]

Participants

5

Reactant 3

HCID 752601-(4-Fluorophenyl)piperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 709812185-Amino-3-(2-fluorophenyl)isoxazol-4-carboxylic acid

Product 1

HCID 70982490(5-Amino-3-(2-fluorophenyl)isoxazol-4-yl)(4-(4-fluorophenyl)piperazine-1-yl)methanoneYield 76.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar manner as described in Example 1, by using dichloromethane (30 mL), 5-amino-3-(2-fluorophenyl)isoxazol-4-carboxylic acid (409 mg, 1.84 mmol), 1-ethyl-3-(dimethylaminopropyl)carbodiimide hydrochloride (388 mg, 2.02 mmol) and 1-(4-fluorophenyl)piperazine (332 mg, 1.84 mmol), a white solid required compound (538 mg, 1.40 mmol, 76%) was obtained.

Sources & evidence

ORD record
ord-9e133714dea14a5881455b6c52cabfc5
Source dataset
uspto-grants-2015_09
Patent number
US09132126B2

Reaction notes

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