3-Methylpyridine → HCID 131732764, compound

HRID 1474428Notes

Reaction equation

[Br:1][C:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[N:4]([C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][N:11]=2)[N:3]=1.[NH2:17][C:18]1[C:23]([Cl:24])=[CH:22][C:21]([Cl:25])=[CH:20][C:19]=1[NH:26][C:27](=[O:30])[O:28][CH3:29].N1C=CC=C(C)C=1.CS(Cl)(=O)=O>CC#N>[Br:1][C:2]1[CH:6]=[C:5]([C:7]([NH:17][C:18]2[C:23]([Cl:24])=[CH:22][C:21]([Cl:25])=[CH:20][C:19]=2[NH:26][C:27](=[O:30])[O:28][CH3:29])=[O:9])[N:4]([C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][N:11]=2)[N:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid (100 mg, 0.33 mmol) and methyl (2-amino-3,5-dichlorophenyl)carbamate prepared in Step 2 (77 mg, 0.33 mmol, 1.0 eq) were mixed with 1 mL of CH3CN. 3-Picoline (0.07 mL, 0.66 mmol, 2.0 eq) was added to the mixture thus obtained, followed by stirring for 30 minutes. After 30 minutes, methanesulfonyl chloride (0.04 mL, 0.5 mmol, 1.5 eq) was slowly added to the mixture. Upon completion of the dropwise addition, the mixture was heated to 40° C. and subjected to a reaction for 24 hours. After confirming the termination of the reaction by using TLC, the solvent was removed, and the residue thus obtained was purified by column chromatography using 20% EtOAc/hexane solution, 50% EtOAc/hexane solution and 100% EtOAc in turn to yield the title compound (130 mg, yield: 75%).

Workup

customthus obtained
waitAfter 30 minutes
additionUpon completion of the dropwise addition
customsubjected to a reaction for 24 hours
customthe termination of the reaction
customthe solvent was removed
customthe residue thus obtained
customwas purified by column chromatography

Sources & evidence

ORD record: ord-d61c42addb8b44fa8ba3d2aec8c477e7
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018233B2

Reaction notes

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