4-Aminotetrahydropyran → 5-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid (tetrahydro-pyran-4-yl)-amide

HRID 1695362Notes

Reaction equation

HRID 1695362 reaction equation
CO[C:3]([C:5]1[NH:6][N:7]=[C:8]([O:10][CH2:11][C:12]2[C:13]([CH2:18][CH2:19][CH2:20][CH3:21])=[N:14][O:15][C:16]=2[CH3:17])[CH:9]=1)=[O:4].COC(C1NN=C(OC[C:33]2[C:34]([C:39]3[CH:44]=CC=CC=3)=[N:35][O:36][C:37]=2C)C=1)=O.NC1CCOCC1>>[O:36]1[CH2:44][CH2:39][CH:34]([NH:35][C:3]([C:5]2[NH:6][N:7]=[C:8]([O:10][CH2:11][C:12]3[C:13]([CH2:18][CH2:19][CH2:20][CH3:21])=[N:14][O:15][C:16]=3[CH3:17])[CH:9]=2)=[O:4])[CH2:33][CH2:37]1

Participants

4

Reactant 3

HCID 4192234-AminotetrahydropyranHCID 66643879HCID 66643879, compoundHCID 66643884HCID 66643884, compound

Product 1

HCID 595684045-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid (tetrahydro-pyran-4-yl)-amideYield 19%

Procedure

As described for example 1b, 5-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid methyl ester (100 mg, 0.34 mmol), instead of 5-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid methyl ester, was converted, using 4-aminotetrahydropyran instead of morpholine, to the title compound (23 mg, 19%) which was obtained as a white solid. MS: m/e=363.0 [M+H]+.

Sources & evidence

ORD record
ord-ce2bb4a92c5d4ecb946d0dfb86bbfacc
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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