N-Aminomorpholine → 5-[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acid morpholin-4-ylamide

HRID 1695335Notes

Reaction equation

HRID 1695335 reaction equation
CO[C:3]([C:5]1[NH:6][N:7]=[C:8]([O:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[CH:9]=1)=[O:4].COC(C1NN=C(OCC2C(C3C=CC=CC=3)=NOC=2C)C=1)=O.[NH2:48][N:49]1[CH2:54][CH2:53][O:52][CH2:51][CH2:50]1>>[N:49]1([NH:48][C:3]([C:5]2[NH:6][N:7]=[C:8]([O:10][CH2:11][C:12]3[C:13]([C:18]4[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=4)=[N:14][O:15][C:16]=3[CH3:17])[CH:9]=2)=[O:4])[CH2:54][CH2:53][O:52][CH2:51][CH2:50]1

Participants

4

Reactant 3

HCID 20315N-AminomorpholineHCID 666438345-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acid methyl esterHCID 66643884HCID 66643884, compound

Product 1

HCID 497929185-[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acid morpholin-4-ylamideYield 37%

Procedure

As described for example 1b, 5-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2H-pyrazole-3-carboxylic acid methyl ester (100 mg, 0.3 mmol), instead of 5-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid methyl ester, was converted, using 4-aminomorpholine instead of morpholine, to the title compound (45 mg, 37%), which was obtained as a colorless oil. MS: m/e=402.3 [M+H]+.

Sources & evidence

ORD record
ord-7ae7d728f4754bbe86ba1b18f5d8d00c
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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