Hydrochloric Acid → 4-(((3S,4S)-4-ethylpyrrolidin-3-yl)amino)-6-(1-phenyl-1H-1,2,3-triazol-4-yl)pyrrolo[1,2-b]pyridazine-3-carboxamide

HRID 877807Notes

Reaction equation

HRID 877807 reaction equation
[C:1]([C:4]1[CH:9]=[N:8][N:7]2[CH:10]=[C:11]([C:13]3[N:14]=[N:15][N:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:17]=3)[CH:12]=[C:6]2[C:5]=1[NH:24][C@H:25]1[C@@H:29]([CH2:30][CH3:31])[CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26]1)(=[O:3])[NH2:2].Cl.O1CCOCC1>ClCCl>[CH2:30]([C@H:29]1[CH2:28][NH:27][CH2:26][C@H:25]1[NH:24][C:5]1[C:6]2[N:7]([CH:10]=[C:11]([C:13]3[N:14]=[N:15][N:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:17]=3)[CH:12]=2)[N:8]=[CH:9][C:4]=1[C:1]([NH2:2])=[O:3])[CH3:31]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 68291098(3S,4S)-tert-butyl 3-((3-carbamoyl-6-(1-phenyl-1H-1,2,3-triazol-4-yl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-4-ethylpyrrolidine-1-carboxylate

Product 1

HCID 682911974-(((3S,4S)-4-ethylpyrrolidin-3-yl)amino)-6-(1-phenyl-1H-1,2,3-triazol-4-yl)pyrrolo[1,2-b]pyridazine-3-carboxamideYield 106.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3S,4S)-tert-butyl 3-((3-carbamoyl-6-(1-phenyl-1H-1,2,3-triazol-4-yl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-4-ethylpyrrolidine-1-carboxylate (41 mg, 0.079 mmol) in dichloromethane (1 mL) was added 4N HCl in 1,4-dioxane (0.198 mL, 0.794 mmol). The solution was stirred at room temperature. After stirring 2 h, the reaction is complete. Concentration afforded a tan solid as the hydrochloride salt of the title compound (35 mg, 99% yield). MS (ES+) m/z: 417.1 (M+H). LC retention time: 2.776 min (analytical LCMS Method J).

Workup

  1. stirringAfter stirring 2 h
  2. concentrationConcentration

Sources & evidence

ORD record
ord-2112761ae6f44104a3095f8e601f4b21
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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