Tetrabutylammonium Fluoride → N-((6-ethynyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)-7-methoxy-1,5-naphthyridin-4-amine

HRID 2176501Notes

Reaction equation

HRID 2176501 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][CH2:14][C:15]3[N:19]4[N:20]=[C:21]([C:24]#[C:25][Si](CC)(CC)CC)[CH:22]=[CH:23][C:18]4=[N:17][N:16]=3)=[CH:8][CH:9]=[N:10]2)=[N:5][CH:4]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C(O)(=O)C>[C:24]([C:21]1[CH:22]=[CH:23][C:18]2[N:19]([C:15]([CH2:14][NH:13][C:7]3[C:6]4[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][N:5]=4)[N:10]=[CH:9][CH:8]=3)=[N:16][N:17]=2)[N:20]=1)#[CH:25]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride2×HCID 576909307-methoxy-N-((6-(2-(triethylsilyl)ethynyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)-1,5-naphthyridin-4-amine

Product 1

HCID 57691226N-((6-ethynyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)-7-methoxy-1,5-naphthyridin-4-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 7-methoxy-N-((6-(2-(triethylsilyl)ethynyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)-1,5-naphthyridin-4-amine (0.360 g, 0.808 mmol) in acetic acid (8 mL) was added TBAF (1.21 ml, 1.21 mmol). The mixture was stirred at room temperature overnight, additional TBAF (1.21 ml, 1.21 mmol) was added and the mixture was heated to 50° C. for five hours. The mixture was concentrated and purified via MPLC (eluted with 0-10% (1:10:90 NH4OH:MeOH:DCM) in dichloromethane) to yield the product as an off-white solid. MS m/z=332.0 [M+1]+. Calc'd for C17H13N7O: 331.1.

Workup

  1. temperaturethe mixture was heated to 50° C. for five hours
  2. concentrationThe mixture was concentrated
  3. custompurified via MPLC (eluted with 0-10% (1:10:90 NH4OH:MeOH:DCM) in dichloromethane)

Sources & evidence

ORD record
ord-7b928b8825904579979698bd4dd065bf
Source dataset
uspto-grants-2015_06
Patent number
US09066954B2

Reaction notes

Loading…