Diisopropylamine → 3-[4-(4-Fluoro-phenyl)-thiazol-2-yl]-N,N-diisopropyl-acrylamide

HRID 1873772Notes

Reaction equation

HRID 1873772 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:13]=[CH:14][C:15]([OH:17])=O)[S:11][CH:12]=2)=[CH:4][CH:3]=1.[CH:18]([NH:21][CH:22]([CH3:24])[CH3:23])([CH3:20])[CH3:19].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([CH:13]=[CH:14][C:15]([N:21]([CH:22]([CH3:24])[CH3:23])[CH:18]([CH3:20])[CH3:19])=[O:17])[S:11][CH:12]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 687134823-[4-(4-Fluoro-phenyl)-thiazol-2-yl]-acrylic Acid

Product 1

HCID 687106003-[4-(4-Fluoro-phenyl)-thiazol-2-yl]-N,N-diisopropyl-acrylamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

98 mg (0.39 mmol) of 3-[4-(4-fluoro-phenyl)-thiazol-2-yl]-acrylic acid, 79.6 mg (0.78 mmol) of diisopropylamine, 119.35 mg (1.17 mmol) of triethylamine and 164.5 mg (0.43 mmol) of HATU in 5 ml of DMF were stirred at room temperature for 2 h. The reaction mixture was concentrated, and water and ethyl acetate were added. The organic phase was separated, washed and evaporated. The residue was purified by chromatography (RP18). Yield: 39 mg.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater and ethyl acetate were added
  3. customThe organic phase was separated
  4. washwashed
  5. customevaporated
  6. customThe residue was purified by chromatography (RP18)

Sources & evidence

ORD record
ord-8da3d2a4f8374f5cad5dfc9b6a610118
Source dataset
uspto-grants-2012_11
Patent number
US08304438B2

Reaction notes

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