Trifluoroacetic acid → HCID 178519661, compound

HRID 1053622Notes

Reaction equation

HRID 1053622 reaction equation
[P:1]([O:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][N:23]([CH2:32][CH:33]2[CH2:36][CH2:35][CH2:34]2)[C:24]([C:26]2[NH:30][N:29]=[C:28]([Cl:31])[CH:27]=2)=[O:25])=[C:18]([F:37])[CH:17]=1)([O:8]C(C)(C)C)([O:3]C(C)(C)C)=[O:2].C(O)(C(F)(F)F)=O.[SiH](CC)(CC)CC>C(#N)C>[P:1]([OH:8])([OH:3])([O:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][N:23]([CH2:32][CH:33]2[CH2:34][CH2:35][CH2:36]2)[C:24]([C:26]2[NH:30][N:29]=[C:28]([Cl:31])[CH:27]=2)=[O:25])=[C:18]([F:37])[CH:17]=1)=[O:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 178454813HCID 178454813, compound

Product 1

HCID 178519661HCID 178519661, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of di-tert-butyl ((4-((3-chloro-N-(cyclobutylmethyl)-1H-pyrazole-5-carboxamido)methyl)-3-fluorophenoxy)methyl) phosphate (0.030 g, 0.054 mmol) in 1 mL ACN was added TFA 0.5 mL and Et3SiH 0.5 mL. After 24 h, the reaction mixture was concentrated. The solvent was removed by evaporation under reduced pressure. Preparative HPLC purification (Water/ACN, 10-100%, 15 min; 100%, 5 min.) provide pure product (4-((3-chloro-N-(cyclobutylmethyl)-1H-pyrazole-5-carboxamido)methyl)-3-fluorophenoxy)methyl dihydrogen phosphate (0.010 g, 0.022 mmol, 42% yield).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customThe solvent was removed by evaporation under reduced pressure
  3. customPreparative HPLC purification (Water/ACN, 10-100%, 15 min; 100%, 5 min.)

Sources & evidence

ORD record
ord-b2dd4863f6464f10bdb48241e88880e5
Source dataset
uspto-grants-2016_07
Patent number
US09394257B2

Reaction notes

Loading…