Diisopropylethylamine → HCID 67404000, compound

HRID 2102053Notes

Reaction equation

HRID 2102053 reaction equation
[Br-].[NH2:2][C:3]1[C:8]([CH2:9][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[C:7]([Cl:29])[C:6]([C:30]#[N:31])=[CH:5][CH:4]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[F:65][C:66]([F:73])([F:72])[CH2:67][CH2:68][C:69](O)=O>CN(C=O)C.C([O-])(O)=O.[Na+]>[Cl:29][C:7]1[C:6]([C:30]#[N:31])=[CH:5][CH:4]=[C:3]2[C:8]=1[CH:9]=[C:69]([CH2:68][CH2:67][C:66]([F:73])([F:72])[F:65])[NH:2]2

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27770854,4,4-Trifluorobutanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86620688HCID 86620688, compound

Product 1

HCID 67404000HCID 67404000, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of {[6-amino-3-cyano-2-(chloro)phenyl]methyl}(triphenyl) phosphonium bromide (Example 234A) (0.20 g, 0.39 mmol), HATU (0.157 g, 0.41 mmol), diisopropylethylamine (0.053 g, 0.41 mmol), and trifluoropropylcarboxylic acid (0.058 g, 0.41 mmol) in DMF (15 mL) was stirred at 100° C. for 24 h. After cooling to rt, the reaction was diluted with NaHCO3 (50 mL) and extracted with EtOAc (100 mL). The organic phase was washed with water and sat'd brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (20-70% EtOAc-hexanes gradient) to afford the title compound as a light yellow solid: MS (ES) m/z 273 (M+1).

Workup

  1. extractionextracted with EtOAc (100 mL)
  2. washThe organic phase was washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (20-70% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-edbc8fc9b4af4e03bb7f7647d0cd76cf
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

Loading…