Hydrochloric Acid → 4-(((3S,4S)-4-ethylpyrrolidin-3-yl)amino)-6-(3-methylisoxazol-5-yl)pyrrolo[1,2-b]pyridazine-3-carboxamide

HRID 877804Notes

Reaction equation

HRID 877804 reaction equation
[C:1]([C:4]1[CH:9]=[N:8][N:7]2[CH:10]=[C:11]([C:13]3[O:17][N:16]=[C:15]([CH3:18])[CH:14]=3)[CH:12]=[C:6]2[C:5]=1[NH:19][C@H:20]1[C@@H:24]([CH2:25][CH3:26])[CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21]1)(=[O:3])[NH2:2].Cl.O1CCOCC1>ClCCl>[CH2:25]([C@H:24]1[CH2:23][NH:22][CH2:21][C@H:20]1[NH:19][C:5]1[C:6]2[N:7]([CH:10]=[C:11]([C:13]3[O:17][N:16]=[C:15]([CH3:18])[CH:14]=3)[CH:12]=2)[N:8]=[CH:9][C:4]=1[C:1]([NH2:2])=[O:3])[CH3:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 68291147(3S,4S)-tert-butyl 3-((3-carbamoyl-6-(3-methylisoxazol-5-yl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-4-ethylpyrrolidine-1-carboxylate

Product 1

HCID 682914004-(((3S,4S)-4-ethylpyrrolidin-3-yl)amino)-6-(3-methylisoxazol-5-yl)pyrrolo[1,2-b]pyridazine-3-carboxamideYield 107.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3S,4S)-tert-butyl 3-((3-carbamoyl-6-(3-methylisoxazol-5-yl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-4-ethylpyrrolidine-1-carboxylate (62 mg, 0.136 mmol) in dichloromethane (1 mL) was added 4N HCl in 1,4-dioxane (0.512 mL, 2.046 mmol). After stirring at room temperature overnight, the deprotection was complete. The volatile were removed in vacuo to afford the hydrochloride salt of the title compound (52 mg, 98% yield) as an off-white solid. MS (ES+) m/z: 355.1 (M+H).

Workup

  1. customThe volatile were removed in vacuo

Sources & evidence

ORD record
ord-40d01b911c4b42e79168c2adb03901a5
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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