Trifluoroacetic acid → Trifluoroacetic acid

HRID 1487323Notes

Reaction equation

HRID 1487323 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)[N:12]=[C:6]2[C:5]=1[NH:19][C@H:20]1[C@@H:24]([CH3:25])[CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21]1)(=[O:3])[NH2:2].[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]>C(Cl)Cl>[CH3:18][N:16]1[CH:17]=[C:13]([C:11]2[N:12]=[C:6]3[C:5]([NH:19][C@H:20]4[C@@H:24]([CH3:25])[CH2:23][NH:22][CH2:21]4)=[C:4]([C:1]([NH2:2])=[O:3])[CH:9]=[N:8][N:7]3[CH:10]=2)[CH:14]=[N:15]1.[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89995644HCID 89995644, compound

Product 2

HCID 6422Trifluoroacetic acidYield 86%HCID 89995478HCID 89995478, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (3S,4S)-tert-butyl 3-((7-carbamoyl-2-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-b]pyridazin-8-yl)amino)-4-methylpyrrolidine-1-carboxylate in DCM (4.5 ml) at 0° C. was added TFA (526 μl, 6.83 mmol) dropwise. The reaction was stirred at 0° C. for 10 minutes and at room temperature for 1.5 h. The reaction solution was concentrated to yield a yellow oil, which was partitioned between ethyl acetate and water. The organic layer was washed with (sat.) sodium chloride, dried with sodium sulfate, filtered and concentrated to give 2-(1-methyl-1H-pyrazol-4-yl)-8-(((3S,4S)-4-methylpyrrolidin-3-yl)amino)imidazo[1,2-b]pyridazine-7-carboxamide, 2 TFA (333.5 mg, 0.587 mmol, 86% yield) as a yellow solid. ESI-MS (analytical LCMS Method B): m/z 341.2 ([M+H]+). HPLC (analytical HPLC Method B) Rt: 1.847 min.

Workup

  1. concentrationThe reaction solution was concentrated
  2. customto yield a yellow oil, which
  3. customwas partitioned between ethyl acetate and water
  4. washThe organic layer was washed with (sat.) sodium chloride
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8431533f36654c57b22c5a3c860d7224
Source dataset
uspto-grants-2016_08
Patent number
US09428511B2

Reaction notes

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