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

HRID 40203Notes

Reaction equation

HRID 40203 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-0886fd727cb644ae9a1fada190a54379
Source dataset
uspto-grants-2013_09
Patent number
US08524900B2

Reaction notes

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