Dimethylformamide → N-[1-(4-chlorophenyl)-5-isopropylpyrazol-4-yl]-2-[2-methyl-4-(trifluoromethyl)-5-vinyl-imidazol-1-yl]pent-4-enamide

HRID 1754374Notes

Reaction equation

HRID 1754374 reaction equation
[CH3:1][C:2]1[N:3]([CH:13]([CH2:17][CH:18]=[CH2:19])[C:14]([OH:16])=O)[C:4]([CH:11]=[CH2:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.CN(C=O)C.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]2[C:36]([CH:37]([CH3:39])[CH3:38])=[C:35]([NH2:40])[CH:34]=[N:33]2)=[CH:28][CH:27]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>O.CCN(CC)CC>[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([N:32]2[C:36]([CH:37]([CH3:38])[CH3:39])=[C:35]([NH:40][C:14](=[O:16])[CH:13]([N:3]3[C:4]([CH:11]=[CH2:12])=[C:5]([C:7]([F:8])([F:9])[F:10])[N:6]=[C:2]3[CH3:1])[CH2:17][CH:18]=[CH2:19])[CH:34]=[N:33]2)=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 664259211-(4-chlorophenyl)-5-(propan-2-yl)-1H-pyrazol-4-amineHCID 867243782-[2-Methyl-4-(trifluoromethyl)-5-vinylimidazol-1-yl]pent-4-enoic acid

Product 1

HCID 86724379N-[1-(4-chlorophenyl)-5-isopropylpyrazol-4-yl]-2-[2-methyl-4-(trifluoromethyl)-5-vinyl-imidazol-1-yl]pent-4-enamideYield 71.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

To 2-[2-methyl-4-(trifluoromethyl)-5-vinylimidazol-1-yl]pent-4-enoic acid (120 mg, 0.42 mmol) was added DMF (3 mL), Et3N (500 μL, excess), 1-(4-chlorophenyl)-5-isopropylpyrazol-4-amine (100 mg, 0.42 mmol), and HATU (250 mg, excess) and the resulting mixture was stirred at room temperature for 1 h. Water (20 mL) was added and the mixture was extracted with EtOAc (2×50 mL). The combined organics were then dried (MgSO4), concentrated in vacuo, and purified by flash chromatography (SiO2, 80% EtOAc/hexanes) to obtain N-[1-(4-chlorophenyl)-5-isopropylpyrazol-4-yl]-2-[2-methyl-4-(trifluoromethyl)-5-vinylimidazol-1-yl]pent-4-enamide (147 mg, 0.3 mmol, 70% yield).

Workup

  1. extractionthe mixture was extracted with EtOAc (2×50 mL)
  2. dry with materialThe combined organics were then dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography (SiO2, 80% EtOAc/hexanes)

Sources & evidence

ORD record
ord-299af22cc8314be9a40fcc01f3713012
Source dataset
uspto-grants-2015_10
Patent number
US09169248B2

Reaction notes

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