Diisopropylethylamine → N-[5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-4-{[(2-methoxyethyl)(methyl)amino]methyl}benzamide

HRID 2382900Notes

Reaction equation

HRID 2382900 reaction equation
Cl[CH2:2][C:3]1[CH:27]=[CH:26][C:6]([C:7]([NH:9][C:10]2[N:25]=[C:13]3[CH:14]=[CH:15][CH:16]=[C:17]([NH:18][CH:19]4[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]4)[N:12]3[N:11]=2)=[O:8])=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.[CH3:37][O:38][CH2:39][CH2:40][NH:41][CH3:42]>O1CCOCC1>[CH:19]1([NH:18][C:17]2[N:12]3[N:11]=[C:10]([NH:9][C:7](=[O:8])[C:6]4[CH:26]=[CH:27][C:3]([CH2:2][N:41]([CH2:40][CH2:39][O:38][CH3:37])[CH3:42])=[CH:4][CH:5]=4)[N:25]=[C:13]3[CH:14]=[CH:15][CH:16]=2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 300977(2-Methoxyethyl)(methyl)amineHCID 252127664-chloromethyl-N-(5-cyclohexylamino-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-benzamide

Product 1

HCID 59437471N-[5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-4-{[(2-methoxyethyl)(methyl)amino]methyl}benzamideYield 4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a reaction vessel containing 4-chloromethyl-N-(5-cyclohexylamino-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-benzamide ((B8), 90 mg, 0.23 mmol, 1 eq.) and N,N-diisopropylethylamine (0.35 mmol, 61 μL, 1.5 eq.) in dioxane (3 mL) was added N-(2-methoxyethyl)methylamine (0.28 mmol, 25 μL, 1.2 eq.) dropwise. The vessel was capped and the reaction stirred at room temperature for 1 hour and heated to 80° C. for a further 15 hours. The solvent was removed in vacuo and the residue dissolved in DMSO (1.5 mL) and purified by reverse phase preparatory HPLC to give the title compound as a light yellow solid (3.9 mg, 4%). HPLC, Rt: 3.46 min (purity: 93%). LC/MS M+(ESI): 437.2, M−(ESI) 435.2.

Workup

  1. customThe vessel was capped
  2. temperatureheated to 80° C. for a further 15 hours
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue dissolved in DMSO (1.5 mL)
  5. custompurified by reverse phase preparatory HPLC

Sources & evidence

ORD record
ord-43fd8de979d1454bb6cc280694dbf9f8
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

Loading…