Ammonia → (S)-6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-3-carboxamide

HRID 521578Notes

Reaction equation

HRID 521578 reaction equation
[CH3:1][N:2]([C@H:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:18])[C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([C:12]([O:14]CC)=O)=[N:10][N:11]=2)[N:8]=1.[NH3:25]>>[CH3:1][N:2]([C@H:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:18])[C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([C:12]([NH2:25])=[O:14])=[N:10][N:11]=2)[N:8]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 117624621(S)-ethyl 6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-3-carboxylate

Product 1

HCID 71115968(S)-6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-3-carboxamideYield 92%

Procedure

A solution of compound (S)-ethyl 6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-3-carboxylate (0.5 g, 1.5 mmol) in 5 mL of methanolic ammonia (7N) was stirred for 0.5 h at room temperature. The mixture was concentrated in vacuum to give product (S)-6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-3-carboxamide as a yellow solid (0.42 g, 92%). LRMS (M+H+) m/z: calcd 297.15; found 297. 1H NMR (300 MHz, CDCl3): δ 8.11 (br, 1H), 8.05-8.02 (d, J=9 Hz, 1H), 7.40-7.29 (m, 5H), 7.13-7.10 (d, J=9 Hz, 1H), 6.47 (br, 1H), 5.57-5.55 (q, 1H), 2.97 (s, 3H), 1.71-1.69 (d, 3H).

Workup

  1. concentrationThe mixture was concentrated in vacuum

Sources & evidence

ORD record
ord-80b14ec30fc746ac95db833d90482515
Source dataset
uspto-grants-2016_05
Patent number
US09328117B2

Reaction notes

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