Trifluoroacetic acid → 2-(2-((2-((1H-Pyrazol-4-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethynyl)phenyl)propanamide

HRID 592461Notes

Reaction equation

HRID 592461 reaction equation
[NH2:1][C:2](=[O:36])[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]#[C:12][C:13]1[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][N:16]=[C:15]([NH:23][C:24]2[CH:25]=[N:26][N:27](C(OC(C)(C)C)=O)[CH:28]=2)[N:14]=1)[CH3:4].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:26]1[CH:25]=[C:24]([NH:23][C:15]2[N:14]=[C:13]([C:12]#[C:11][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[CH:3]([CH3:4])[C:2]([NH2:1])=[O:36])[C:18]([C:19]([F:21])([F:20])[F:22])=[CH:17][N:16]=2)[CH:28]=[N:27]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86712335tert-Butyl 4-((4-((2-(1-amino-1-oxopropan-2-yl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-1H-pyrazole-1-carboxylate

Product 1

HCID 867123362-(2-((2-((1H-Pyrazol-4-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethynyl)phenyl)propanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 4-((4-((2-(1-amino-1-oxopropan-2-yl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-1H-pyrazole-1-carboxylate A62 (0.31 g, 0.62 mmol) and TFA (0.90 mL, 12 mmol) in DCM (3.0 mL) was stirred for 2 hours at room temperature. The mixture was concentrated under reduced pressure and diluted with water (50 mL) before extracting with DCM (2×50 mL) and EtOAc (50 mL). The combined organic residues were concentrated and purified using silica gel column chromatography (50-100% EtOAc in petroleum benzine 40-60° C. then 0-10% MeOH in EtOAc) to give the title compound A63 (0.211 g, 85%). LCMS-D: rt 3.162 min; m/z 401.2 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiondiluted with water (50 mL)
  3. extractionbefore extracting with DCM (2×50 mL) and EtOAc (50 mL)
  4. concentrationThe combined organic residues were concentrated
  5. custompurified
  6. custom50-100% EtOAc in petroleum benzine 40-60° C.

Sources & evidence

ORD record
ord-87a2c92a7532411f97c4abb67668c24c
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

Loading…