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

HRID 219092Notes

Reaction equation

HRID 219092 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-d56717f05c344e288c80cf5d62ede020
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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