Hydrochloric Acid → 2-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-(2-methoxy-ethoxymethyl)-2H-pyrazole-3-carboxylic acid

HRID 33263Notes

Reaction equation

[Cl:1][C:2]1[S:6][C:5]([C:7]2[O:11][N:10]=[C:9]([CH2:12][N:13]3[C:17]([C:18]([OH:20])=[O:19])=[CH:16][C:15]([CH2:21][OH:22])=[N:14]3)[CH:8]=2)=[CH:4][CH:3]=1.Br[CH2:24][CH2:25][O:26][CH3:27].Cl>CN(C=O)C>[Cl:1][C:2]1[S:6][C:5]([C:7]2[O:11][N:10]=[C:9]([CH2:12][N:13]3[C:17]([C:18]([OH:20])=[O:19])=[CH:16][C:15]([CH2:21][O:22][CH2:24][CH2:25][O:26][CH3:27])=[N:14]3)[CH:8]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 500 mg of 2-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-hydroxymethyl-2H-pyrazole-3-carboxylic acid in 5 ml DMF 480 mg Cs2CO3 and 204 mg 1-Bromo-2-methoxy-ethane were added and the mixture was heated to 80° C. for 5 h. Then the mixture was acidified to pH 4 with aqueous HCl and filtered through a chem elut® cartridge by elution with ethyl acetate. After concentration the crude product was directly subjected to the next reaction step.

Workup

filtrationfiltered through a chem elut® cartridge by elution with ethyl acetate
concentrationAfter concentration the crude product
customwas directly subjected to the next reaction step

Sources & evidence

ORD record: ord-a547fe0344f84561a66ac7a3a0247452
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429581B2

Reaction notes

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