Diisopropylethylamine → HCID 57657933, compound

HRID 391576Notes

Reaction equation

HRID 391576 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O)#[CH:2].[CH3:12][N:13]1[C:17]([NH2:18])=[CH:16][C:15]([CH3:19])=[N:14]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH3:12][N:13]1[C:17]([NH:18][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([C:1]#[CH:2])[CH:4]=2)=[CH:16][C:15]([CH3:19])=[N:14]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 5207211,3-Dimethyl-1H-pyrazol-5-amineHCID 158970473-Ethynylbenzoic acid

Product 1

HCID 57657933HCID 57657933, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

3-Ethynylbenzoic acid (0.1 g, 0.685 mmol) was added to a dry 50 mL round bottom flask and dissolved in DMF (6.85 mL). To the resulting solution was added 1,3-dimethyl-1H-pyrazol-5-amine (0.076 g, 0.685 mmol), followed by BOP (0.393 g, 0.890 mmol), and 0.238 mL of DIPEA (1.37 mmol). This reaction mixture was heated to 50° C. for 3 h. After allowing the reaction to cool to room temperature it was taken up in EtOAc (15 mL) and extracted with brine (3×15 mL). The EtOAc layer was then washed with saturated aqueous NaHCO3 (2×15 mL). The organics were dried over anhydrous Na2SO4(s), filtered and concentrated in vacuo. The crude residue was purified via column chromatography (silica gel, gradient eluant mixture of EtOAc in Hexanes: 0% to 100% EtOAc) affording N-(1,3-dimethyl-1H-pyrazol-5-yl)-3-ethynylbenzamide (0.128 g, 78%).

Workup

  1. customthe reaction
  2. temperatureto cool to room temperature it
  3. extractionextracted with brine (3×15 mL)
  4. washThe EtOAc layer was then washed with saturated aqueous NaHCO3 (2×15 mL)
  5. dry with materialThe organics were dried over anhydrous Na2SO4(s)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified via column chromatography (silica gel, gradient eluant mixture of EtOAc in Hexanes: 0% to 100% EtOAc)

Sources & evidence

ORD record
ord-e6f2ec7eaedb47749aea93d3cfbefb1d
Source dataset
uspto-grants-2013_02
Patent number
US08383825B2

Reaction notes

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