Trifluoroacetic acid → 4-(((3R,4R)-3-ethylpiperidin-4-yl)amino)-6-(1-methyl-1H-pyrazol-4-yl)pyrrolo[1,2-b]pyridazine-3-carboxamide

HRID 877759Notes

Reaction equation

HRID 877759 reaction equation
[C:1]([C:4]1[CH:9]=[N:8][N:7]2[CH:10]=[C:11]([C:13]3[CH:14]=[N:15][N:16]([CH3:18])[CH:17]=3)[CH:12]=[C:6]2[C:5]=1[NH:19][C@@H:20]1[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][C@H:21]1[CH2:33][CH3:34])(=[O:3])[NH2:2].FC(F)(F)C(O)=O>ClCCl>[CH2:33]([C@H:21]1[C@H:20]([NH:19][C:5]2[C:6]3[N:7]([CH:10]=[C:11]([C:13]4[CH:14]=[N:15][N:16]([CH3:18])[CH:17]=4)[CH:12]=3)[N:8]=[CH:9][C:4]=2[C:1]([NH2:2])=[O:3])[CH2:25][CH2:24][NH:23][CH2:22]1)[CH3:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68291150(3R,4R)-tert-butyl 4-((3-carbamoyl-6-(1-methyl-1H-pyrazol-4-yl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-3-ethylpiperidine-1-carboxylate

Product 1

HCID 682916234-(((3R,4R)-3-ethylpiperidin-4-yl)amino)-6-(1-methyl-1H-pyrazol-4-yl)pyrrolo[1,2-b]pyridazine-3-carboxamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3R,4R)-tert-butyl 4-((3-carbamoyl-6-(1-methyl-1H-pyrazol-4-yl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-3-ethylpiperidine-1-carboxylate (288 mg, 0.618 mmol) in dichloromethane (5.0 ml) cooled to 0° C. was added trifluoroacetic acid (288 μl, 3.74 mmol). The reaction was allowed to warm to room temperature and stirring was continued for 1 hr. After removal of the solvent in vacuo, the residue was diluted with ethyl acetate, washed successively with saturated sodium bicarbonate, water, and brine; dried with sodium sulfate, filtered, and concentrated under reduced pressure, yielding 4-(((3R,4R)-3-ethylpiperidin-4-yl)amino)-6-(1-methyl-1H-pyrazol-4-yl)pyrrolo[1,2-b]pyridazine-3-carboxamide (227 mg, 0.618 mmol, 99% yield) as a white solid. LCMS (Method K) m/z 368.4 ([M+H]+).

Workup

  1. customAfter removal of the solvent in vacuo
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed successively with saturated sodium bicarbonate, water, and brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d6ed41a4258741969d72cc7686e16af7
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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