p-Toluenesulfonic acid monohydrate → HCID 73294786, compound

HRID 592432Notes

Reaction equation

HRID 592432 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([CH3:21])([CH3:20])[C:17]([NH2:19])=[O:18])[C:5]([Cl:22])=[CH:4][N:3]=1.[CH3:23][N:24]1[CH:28]=[C:27]([NH2:29])[CH:26]=[N:25]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[Cl:22][C:5]1[C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([CH3:21])([CH3:20])[C:17]([NH2:19])=[O:18])=[N:7][C:2]([NH:29][C:27]2[CH:26]=[N:25][N:24]([CH3:23])[CH:28]=2)=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 47709901-methyl-1H-pyrazol-4-amineHCID 86712313HCID 86712313, compound

Product 1

HCID 73294786HCID 73294786, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-(2-(2-(2,5-dichloropyrimidin-4-yl)ethyl)phenyl)-2-methylpropanamide A38 (0.042 g, 0.12 mmol), 1-methyl-1H-pyrazol-4-amine (0.022 g, 0.23 mmol), and p-toluenesulfonic acid monohydrate (0.002 g, 0.012 mmol) in 1,4-dioxane (4.0 mL) was heated in the microwave at 120° C. for 3 hours. After cooling, the volatiles were removed in vacuo and the residue was adsorbed onto silica. Purification by column chromatography (Biotage Isolera, 12 g SiO2, 0-5% MeOH in DCM) gave the title compound 45 as an off-white solid (0.009 g, 18%). LCMS-D: rt 3.29 min; m/z 399 [M+H]+.

Workup

  1. temperatureAfter cooling
  2. customthe volatiles were removed in vacuo
  3. customPurification by column chromatography (Biotage Isolera, 12 g SiO2, 0-5% MeOH in DCM)

Sources & evidence

ORD record
ord-aef0cdf0ef3b4941b790b575daf8c8b4
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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