L-Alaninol → 2-Methyl-5-(5-methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid ((S)-2-hydroxy-1-methyl-ethyl)-amide

HRID 1695411Notes

Reaction equation

HRID 1695411 reaction equation
CO[C:3]([C:5]1[N:6]([CH3:24])[N:7]=[C:8]([O:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[CH:9]=1)=[O:4].C[O:26][C:27]([C:29]1[NH:30]N=C(OCC2C(C3C=CC=CC=3)=NOC=2C)[CH:33]=1)=O.N[C@H](CO)C>>[OH:26][CH2:27][C@@H:29]([NH:30][C:3]([C:5]1[N:6]([CH3:24])[N:7]=[C:8]([O:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[CH:9]=1)=[O:4])[CH3:33]

Participants

4

Reactant 3

HCID 80307L-AlaninolHCID 66643749HCID 66643749, compoundHCID 66643884HCID 66643884, compound

Product 1

HCID 666438212-Methyl-5-(5-methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid ((S)-2-hydroxy-1-methyl-ethyl)-amideYield 89%

Procedure

As described for example 6, 2-methyl-5-(5-methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid methyl ester (90 mg, 0.27 mmol), instead of 5-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid methyl ester, was converted, using L-alaninol instead of ethanolamine, to the title compound (91 mg, 89%) which was obtained as a colorless oil. MS: m/e=372.2 [M+H]+.

Sources & evidence

ORD record
ord-fe513ac962194ea4bd378113ccae8a57
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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