p-(1-Piperazinyl)phenol → (5-Amino-3-(2-fluorophenyl)isoxazol-4-yl)(4-(4-hydroxyphenyl)piperazine-1-yl)methanone

HRID 2276480Notes

Reaction equation

HRID 2276480 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.OC1C2N=NNC=2C=CC=1.[N:39]1([C:45]2[CH:50]=[CH:49][C:48]([OH:51])=[CH:47][CH:46]=2)[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1>>[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:42]1[CH2:41][CH2:40][N:39]([C:45]2[CH:46]=[CH:47][C:48]([OH:51])=[CH:49][CH:50]=2)[CH2:44][CH2:43]1)=[O:16]

Participants

5

Reactant 4

HCID 92467p-(1-Piperazinyl)phenolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 709812185-Amino-3-(2-fluorophenyl)isoxazol-4-carboxylic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 70981250(5-Amino-3-(2-fluorophenyl)isoxazol-4-yl)(4-(4-hydroxyphenyl)piperazine-1-yl)methanoneYield 59%

Procedure

In a similar manner as described in Example 1, by using dimethylformimide (15 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), hydroxybenzotriazole (299 mg, 2.21 mmol) and 4-(piperazine-1-yl)phenol (328 mg, 1.84 mmol), a white solid required compound (412 mg, 1.08 mmol, 59%) was obtained.

Sources & evidence

ORD record
ord-f6e0bf97d51d412c8b087391d6e64610
Source dataset
uspto-grants-2015_09
Patent number
US09132126B2

Reaction notes

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