Trifluoroacetic acid → (6-(3-Methylisoxazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methanamine

HRID 2176503Notes

Reaction equation

HRID 2176503 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([CH2:16][NH:17]C(=O)OC(C)(C)C)=[N:14][N:15]=3)[N:12]=2)[O:4][N:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([CH2:16][NH2:17])=[N:14][N:15]=3)[N:12]=2)[O:4][N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57691036Tert-butyl (6-(3-methylisoxazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

Product 1

HCID 57691348(6-(3-Methylisoxazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methanamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (6-(3-methylisoxazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate (3.63 g, 11.0 mmol) in dichloromethane (50 mL) was added trifluoroacetic acid (16.9 ml, 220 mmol) and the mixture was stirred at room temperature for one hour. The mixture was concentrated, taken up in a solution of ammonia in methanol (2.0 M) and purified by MPLC chromatography (eluted with 0-10% (1:10:90 NH4OH:MeOH:DCM) in DCM) to yield the product as a brown solid. MS m/z=230.8 [M+1]+. Calc'd for C10H10N6O: 230.1.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by MPLC chromatography (eluted with 0-10% (1:10:90 NH4OH:MeOH:DCM) in DCM)

Sources & evidence

ORD record
ord-575fbe183cfb43358af08c5dc3cd5333
Source dataset
uspto-grants-2015_06
Patent number
US09066954B2

Reaction notes

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