Triethylamine → HCID 66785186, compound

HRID 1020848Notes

Reaction equation

HRID 1020848 reaction equation
[Cl:1][C:2]1[C:3]([NH:9][NH2:10])=[N:4][CH:5]=[CH:6][C:7]=1[I:8].C(N(CC)CC)C.[F:18][C:19]([F:25])([F:24])[CH2:20][C:21](Cl)=[O:22].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[C:3]([NH:9][NH:10][C:21](=[O:22])[CH2:20][C:19]([F:25])([F:24])[F:18])=[N:4][CH:5]=[CH:6][C:7]=1[I:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 27833433,3,3-Trifluoropropionyl chlorideHCID 57459596HCID 57459596, compound

Product 1

HCID 66785186HCID 66785186, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of intermediate compound D7 (2.528 g, 9.38 mmol) in dry DCM (15 ml), cooled at 0° C., were added triethylamine (3.244 ml, 23.45 mmol) and 3,3,3,-trifluoropropionyl chloride (1.924 g, 13.132 mmol). The resulting reaction mixture was stirred at r.t. for 3 h. After this period, NaHCO3 (aqueous sat. solution) was added. The resulting solution was then extracted with DCM. The organic layer was separated, dried (MgSO4) and concentrated in vacuo. The residue thus obtained was triturated with DIPE to yield intermediate compound D10 (4 g, 55%).

Workup

  1. customThe resulting reaction mixture
  2. waitAfter this period
  3. extractionThe resulting solution was then extracted with DCM
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue thus obtained
  8. customwas triturated with DIPE
  9. customto yield intermediate compound D10 (4 g, 55%)

Sources & evidence

ORD record
ord-ff1dae029e0948a5a210546aa2c69f55
Source dataset
uspto-grants-2014_05
Patent number
US08716480B2

Reaction notes

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