2-Dimethylaminopyridine → 2-(6-Bromopyridin-2-yl)-2-methyl-N-(1-methyl-1-H-pyrazol-4-yl)propanamide

HRID 385915Notes

Reaction equation

HRID 385915 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([CH3:13])([CH3:12])[C:9]([OH:11])=O)[CH:5]=[CH:4][CH:3]=1.[CH3:14][N:15]1[CH:19]=[C:18]([NH2:20])[CH:17]=[N:16]1.CN(C1C=CC=CN=1)C.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[Br:1][C:2]1[N:7]=[C:6]([C:8]([CH3:13])([CH3:12])[C:9]([NH:20][C:18]2[CH:17]=[N:16][N:15]([CH3:14])[CH:19]=2)=[O:11])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 47709901-methyl-1H-pyrazol-4-amineHCID 595262532-(6-Bromopyridin-2-yl)-2-methylpropanoic acid

Product 1

HCID 595262622-(6-Bromopyridin-2-yl)-2-methyl-N-(1-methyl-1-H-pyrazol-4-yl)propanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(6-bromopyridin-2-yl)-2-methylpropanoic acid (120 mg, 0.49 mmol) in dimethylformamide (3 mL) was charged with 1-methyl-1H-pyrazol-4-amine (48 mg, 0.49 mmol). Dimethylaminopyridine (60 mg, 0.49 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (94 mg, 0.49 mmol) were added and the reaction was stirred overnight at room temperature. The reaction was purified by reverse phase HPLC (10-100% acetonitrile/water+0.05% TFA modifier) to afford the title compound.

Workup

  1. customThe reaction was purified by reverse phase HPLC (10-100% acetonitrile/water+0.05% TFA modifier)

Sources & evidence

ORD record
ord-c5a1cd9f14c543519d5f8b155899ff81
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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