p-Toluenesulfonic acid → HCID 66690481, compound

HRID 592291Notes

Reaction equation

HRID 592291 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[N:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].Br[CH2:23][CH:24](OC)OC.CC1C=CC(S(O)(=O)=O)=CC=1>CN(C)C=O>[CH3:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]2[N:14]3[CH:23]=[CH:24][N:1]=[C:2]3[CH:3]=[C:4]([C:5]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:6])[CH:12]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 816722-Bromo-1,1-dimethoxyethaneHCID 66690453HCID 66690453, compound

Product 1

HCID 66690481HCID 66690481, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of tert-butyl 2-amino-6-(4-methylphenyl)isonicotinate (57 mg, 0.2 mmol) in N,N-dimethylformamide (1.3 mL) were added 2-bromo-1,1-dimethoxyethane (33.9 mg, 0.2 mmol) and 4-methylbenzenesulfonic acid (5.2 mg, 0.03 mmol). The mixture was heated to 90° C. After 18 h, the mixture was filtered. The filtrate was purified by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.025% trifluoroacetic acid) gave the title compound (30 mg): LC-MS [M+1]=309.2.

Workup

  1. filtrationthe mixture was filtered
  2. customThe filtrate was purified by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.025% trifluoroacetic acid)

Sources & evidence

ORD record
ord-4ff93981bff240c48ba612e9c8eab574
Source dataset
uspto-grants-2016_01
Patent number
US09238647B2

Reaction notes

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