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

HRID 2276481Notes

Reaction equation

HRID 2276481 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][CH:48]=[CH:47][C:46]=2[OH:51])[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:50]=[CH:49][CH:48]=[CH:47][C:46]=2[OH:51])[CH2:44][CH2:43]1)=[O:16]

Participants

5

Reactant 4

HCID 70530o-(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 70981197(5-Amino-3-(2-fluorophenyl)isoxazol-4-yl)(4-(2-hydroxyphenyl)piperazine-1-yl)methanoneYield 62.5%

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 2-(piperazine-1-yl)phenol (328 mg, 1.84 mmol), a white solid required compound (439 mg, 1.15 mmol, 62%) was obtained.

Sources & evidence

ORD record
ord-a68465228bf64d1bab6683d922bb8687
Source dataset
uspto-grants-2015_09
Patent number
US09132126B2

Reaction notes

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