Isopropylamine → HCID 67359702, compound

HRID 404398Notes

Reaction equation

HRID 404398 reaction equation
[CH3:1][C:2]([CH3:26])([CH3:25])[C:3]([O:5][CH2:6][C:7]1[CH:8]=[C:9]([C:22]([OH:24])=O)[C:10]([C:13]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=2[F:21])=[CH:11][CH:12]=1)=[O:4].S(Cl)(Cl)=O.[CH:31]([NH2:34])([CH3:33])[CH3:32]>C(Cl)Cl.CN(C=O)C>[CH3:25][C:2]([CH3:1])([CH3:26])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=2[F:21])=[C:9]([C:22]([NH:34][CH:31]([CH3:33])[CH3:32])=[O:24])[CH:8]=1)=[O:4]

Participants

6

Reactant 3

HCID 6363IsopropylamineHCID 24386Thionyl ChlorideHCID 67360689HCID 67360689, compound

Product 1

HCID 67359702HCID 67359702, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a room temperature solution of 29.2 (432 mg, 1199 μmol) in DCM (6.0 mL) was added two drops of DMF followed by thionyl chloride (0.26 mL, 3596 μmol). The mixture was refluxed under N2 for 1.5 hours, cooled to room temperature, and the organic solvent was removed under reduced pressure. The residue was treated with neat isopropylamine (2.0 mL, 23515 μmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA), and the mixture was heated at 50° C. for 45 minutes. The reaction was then quenched with water (5 mL) and extracted with (3×5 mL) EtOAc. After removal of organic solvents under reduced pressure, purification of the residue by flash chromatography on silica gel with 0-50% EtOAc/hexanes for elution gave 29.3 as white solid (378 mg, 79%).

Workup

  1. temperatureThe mixture was refluxed under N2 for 1.5 hours
  2. customthe organic solvent was removed under reduced pressure
  3. temperature, USA), and the mixture was heated at 50° C. for 45 minutes
  4. customThe reaction was then quenched with water (5 mL)
  5. extractionextracted with (3×5 mL) EtOAc
  6. customAfter removal of organic solvents
  7. customunder reduced pressure, purification of the residue by flash chromatography on silica gel with 0-50% EtOAc/hexanes
  8. washfor elution

Sources & evidence

ORD record
ord-d3775f8ca645412c88cf894b579f0188
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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