Trifluoroacetic acid → HCID 58608422, compound

HRID 1627581Notes

Reaction equation

HRID 1627581 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([O:12][C:13]1[C:14]([NH2:32])=[N:15][CH:16]=[C:17]([C:19]2[CH:20]=[N:21][N:22]([CH2:24][CH:25]3[CH2:29][O:28]C(C)(C)[O:26]3)[CH:23]=2)[CH:18]=1)[CH3:11].C(O)(C(F)(F)F)=O>C1COCC1.O>[NH2:32][C:14]1[N:15]=[CH:16][C:17]([C:19]2[CH:20]=[N:21][N:22]([CH2:24][CH:25]([OH:26])[CH2:29][OH:28])[CH:23]=2)=[CH:18][C:13]=1[O:12][CH:10]([C:3]1[C:4]([Cl:9])=[CH:5][CH:6]=[C:7]([F:8])[C:2]=1[Cl:1])[CH3:11]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58608421HCID 58608421, compound

Product 1

HCID 58608422HCID 58608422, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-5-[1-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrazol-4-yl]-pyridin-2-ylamine (150 mg, 0.31 mmol) in THF (3 mL) and H2O (2 mL) was added TFA (2 mL) at 0° C., the mixture was stirred and warmed to room temperature, then heated at 50° C. for 5 hours, LCMS checked that the reaction was completed, remove THF, the residue was purified by prep-HPLC to leave 3-(4-{6-amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-3-yl}-pyrazol-1-yl)-propane-1,2-diol (102 mg), yield 74.2%.

Workup

  1. temperatureheated at 50° C. for 5 hours
  2. customremove THF
  3. customthe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-7dad35e404a64c1f80bc2ce324c4dbb8
Source dataset
uspto-grants-2014_07
Patent number
US08785632B2

Reaction notes

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