Isobutylamine → 4-Amino-N-[2-(isobutylamino)ethyl]-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-7,8-dihydro-2H-6-thia-1,2,3,5-tetraazaacenaphthylene-7-carboxamide

HRID 1693278Notes

Reaction equation

HRID 1693278 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]2[C:13]3[C:7]([CH2:8][CH:9]([C:14]([NH:16][CH2:17][CH2:18]Cl)=[O:15])[S:10][C:11]=3[N:12]=1)=[N:6][N:5]2[CH2:20][C:21]1[C:26]([CH3:27])=[C:25]([O:28][CH3:29])[C:24]([CH3:30])=[CH:23][N:22]=1.[CH2:31]([NH2:35])[CH:32]([CH3:34])[CH3:33]>O1CCOCC1>[NH2:1][C:2]1[N:3]=[C:4]2[C:13]3[C:7]([CH2:8][CH:9]([C:14]([NH:16][CH2:17][CH2:18][NH:35][CH2:31][CH:32]([CH3:34])[CH3:33])=[O:15])[S:10][C:11]=3[N:12]=1)=[N:6][N:5]2[CH2:20][C:21]1[C:26]([CH3:27])=[C:25]([O:28][CH3:29])[C:24]([CH3:30])=[CH:23][N:22]=1

Participants

4

Reactant 2

HCID 6558IsobutylamineHCID 593114214-Amino-N-(2-chloroethyl)-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-7,8-dihydro-2H-6-thia-1,2,3,5-tetraazaacenaphthylene-7-carboxamide

Product 1

HCID 593115264-Amino-N-[2-(isobutylamino)ethyl]-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-7,8-dihydro-2H-6-thia-1,2,3,5-tetraazaacenaphthylene-7-carboxamideYield 28%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture composed of 4-amino-N-(2-chloroethyl)-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-7,8-dihydro-2H-6-thia-1,2,3,5-tetraazaacenaphthylene-7-carboxamide of Example 16 (20 mg), isobutylamine (0.8 mL) and dioxane (3 mL) was heated under reflux for 16 hours, and then the reaction mixture was concentrated under reduced pressure. The resulting residue was purified by reversed phase liquid chromatography to obtain the title compound (6 mg, 28%) as a solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customThe resulting residue was purified by reversed phase liquid chromatography

Sources & evidence

ORD record
ord-5047bebc846a4beeb484a079586b4651
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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