Trifluoroacetic acid → Trifluoroacetic acid

HRID 1487334Notes

Reaction equation

HRID 1487334 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]([CH2:18][CH3:19])[CH:17]=3)[N:12]=[C:6]2[C:5]=1[NH:20][C@H:21]1[C@@H:25]([CH2:26][F:27])[CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22]1)(=[O:3])[NH2:2].[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36]>C(Cl)Cl>[CH2:18]([N:16]1[CH:17]=[C:13]([C:11]2[N:12]=[C:6]3[C:5]([NH:20][C@H:21]4[C@@H:25]([CH2:26][F:27])[CH2:24][NH:23][CH2:22]4)=[C:4]([C:1]([NH2:2])=[O:3])[CH:9]=[N:8][N:7]3[CH:10]=2)[CH:14]=[N:15]1)[CH3:19].[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89995501HCID 89995501, compound

Product 2

HCID 6422Trifluoroacetic acidYield 79%HCID 89995502HCID 89995502, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (3S,4S)-tert-butyl 3-((7-carbamoyl-2-(1-ethyl-1H-pyrazol-4-yl)imidazo[1,2-b]pyridazin-8-yl)amino)-4-(fluoromethyl)pyrrolidine-1-carboxylate (15 mg, 0.032 mmol) in DCM (0.5 ml) was treated with TFA (0.024 ml, 0.317 mmol) at room temperature for 2 h. The reaction mixture was concentrated to give 2-(1-ethyl-1H-pyrazol-4-yl)-8-(((3S,4S)-4-(fluoromethyl)pyrrolidin-3-yl)amino)imidazo[1,2-b]pyridazine-7-carboxamide, 2 TFA (15.1 mg, 0.025 mmol, 79% yield) as a white solid. ESI-MS (Method A): m/z 373.3 ([M+H]+).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-be8b4c4f91a24557940d20a682977260
Source dataset
uspto-grants-2016_08
Patent number
US09428511B2

Reaction notes

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