p-Toluenesulfonic acid monohydrate → HCID 73297041, compound

HRID 592408Notes

Reaction equation

HRID 592408 reaction equation
[F:1][C:2]([F:11])([F:10])[CH2:3][N:4]1[CH:8]=[C:7]([NH2:9])[CH:6]=[N:5]1.Cl[C:13]1[N:18]=[C:17]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]2([C:30]([NH2:32])=[O:31])[CH2:29][CH2:28]2)[C:16]([Cl:33])=[CH:15][N:14]=1.CC1C=CC(S(O)(=O)=O)=CC=1.O>O1CCOCC1>[Cl:33][C:16]1[C:17]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]2([C:30]([NH2:32])=[O:31])[CH2:29][CH2:28]2)=[N:18][C:13]([NH:9][C:7]2[CH:6]=[N:5][N:4]([CH2:3][C:2]([F:1])([F:10])[F:11])[CH:8]=2)=[N:14][CH:15]=1

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 70159181-(2,2,2-trifluoroethyl)-1H-pyrazol-4-amineHCID 867122951-(2-(2-(2,5-Dichloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide

Product 1

HCID 73297041HCID 73297041, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-amine (0.160 g, 0.967 mmol), 1-(2-(2-(2,5-dichloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide A14 (0.101 g, 0.300 mmol) and TsOH.H2O (0.010 g, 0.051 mmol) in 1,4-dioxane (2.0 mL) was heated to 120° C. for 3 hours in the microwave. The mixture was concentrated under reduced pressure and purified using silica gel column chromatography (0-100% EtOAc in petroleum benzine 40-60° C.) to give the title compound 29 (0.036 g, 26%). LCMS-D: rt 3.402 min; m/z 465.2 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. custompurified
  3. customsilica gel column chromatography (0-100% EtOAc in petroleum benzine 40-60° C.)

Sources & evidence

ORD record
ord-10c4f14b31eb42e685ab1d90b88a763f
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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