Hydrochloric Acid → (S)-N6, 3-dimethyl-N6-(1-phenylethyl)-[1,2,4]triazolo[4,3-b]pyridazine-6,8-diamine
Reaction equation
[CH3:1][C:2]1[N:6]2[N:7]=[C:8]([N:19]([CH3:28])[C@H:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH3:21])[CH:9]=[C:10]([NH:11]C(=O)OC(C)(C)C)[C:5]2=[N:4][N:3]=1.Cl>C1COCC1>[CH3:28][N:19]([C@H:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:21])[C:8]1[CH:9]=[C:10]([NH2:11])[C:5]2[N:6]([C:2]([CH3:1])=[N:3][N:4]=2)[N:7]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of compound (S)-tert-butyl 3-methyl-6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazin-8-ylcarbamate (55 mg) in THF (10 mL) was added 6 N HCl (2 mL) dropwise under ice bath and then stirred at room temperature for 2 hrs. The mixture was quenched by saturated aqueous sodium bicarbonate solution (30 mL) and extracted with EA (20 mL×3). The combined organic layers were dried over Na2SO4, concentrated in vacuum to give product (S)-N6, 3-dimethyl-N6-(1-phenylethyl)-[1,2,4]triazolo[4,3-b]pyridazine-6,8-diamine (Compound 6) as a yellow solid (30 mg, 73.9%). 1H NMR (300 MHz, CD3OD) δ: 7.22˜7.25 (m, 4H), 7.15˜7.18 (m, 1H), 6.30 (s, 12H), 5.69˜5.72 (q, 1H), 2.79 (s, 3H), 2.68 (s, 3H),1.53 (d, 3H, J=4.8 Hz). LRMS (M+H+) m/z: calcd 283; found 283.
Workup
- customThe mixture was quenched by saturated aqueous sodium bicarbonate solution (30 mL)
- extractionextracted with EA (20 mL×3)
- dry with materialThe combined organic layers were dried over Na2SO4
- concentrationconcentrated in vacuum
Sources & evidence
- ORD record
- ord-59bbc289c987444a8db77e45ac84c5f1
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09328117B2
Reaction notes
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