Diisopropylethylamine → HCID 67404000, compound

HRID 1188547Notes

Reaction equation

HRID 1188547 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-65a75db2058841438b30a46472d9c330
Source dataset
uspto-grants-2014_03
Patent number
US08673948B2

Reaction notes

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