Triethylamine → HCID 19047185, compound

HRID 1780598Notes

Reaction equation

HRID 1780598 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([CH3:12])([CH3:11])[CH2:8][CH2:7][S:6](=[O:14])(=[O:13])[C:5]=2[S:4][C:3]=1[C:15]([OH:17])=[O:16].C(Cl)(=O)C(Cl)=O.[CH2:24]([N:26]1[C:30](O)=[CH:29][CH:28]=[N:27]1)[CH3:25].C(N(CC)CC)C>CN(C)C=O.C(Cl)Cl>[CH3:1][C:2]1[C:10]2[C:9]([CH3:12])([CH3:11])[CH2:8][CH2:7][S:6](=[O:13])(=[O:14])[C:5]=2[S:4][C:3]=1[C:15]([O:17][C:30]1[N:26]([CH2:24][CH3:25])[N:27]=[CH:28][CH:29]=1)=[O:16]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 67712506HCID 67712506, compoundHCID 178418331HCID 178418331, compound

Product 1

HCID 19047185HCID 19047185, compoundYield 58.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2.0 g (0.0073 mol) of the title compound of Step D of Example 1 was added to 50 mL of methylene chloride. 1.27 mL (0.0146 mol) of oxalyl chloride (purchased from Janssen) was added followed by 2 drops of N,N-dimethylformamide. The mixture was refluxed under nitrogen for 2 h and was then evaporated to dryness. 50 mL of methylene chloride was added to the residue and evaporated to dryness. Another 50 mL of methylene chloride was added to the residue and the solution was cooled to about 0° C. 0.90 g (0.0080 mol) of 1-ethyl-1H-pyrazol-5-ol was added to the mixture followed by 2.8 mL (0.0020 mol) of triethylamine and the mixture was stirred overnight while warming to room temperature. The mixture was evaporated to dryness. The residue was stirred in 100 mL of water and the water was decanted. The residue was washed with hexane (2×100 mL) and then chromatographed on silica gel eluting with 4:6 ethyl acetate/hexane to yield 1.57 g of the title compound of Step A as a solid melting at 119°-120° C. 1H NMR (CDCl3): δ 1.4 (t, 3H), 1.5 (s, 6H), 2.5 (m, 2H), 2.8 (s, 3H), 3.4 (m, 2H), 4.1 (q, 2H), 6.2 (d, 1H), 7.5 (d, 1H).

Workup

  1. temperatureThe mixture was refluxed under nitrogen for 2 h
  2. customwas then evaporated to dryness
  3. addition50 mL of methylene chloride was added to the residue
  4. customevaporated to dryness
  5. additionAnother 50 mL of methylene chloride was added to the residue
  6. temperaturewhile warming to room temperature
  7. customThe mixture was evaporated to dryness
  8. stirringThe residue was stirred in 100 mL of water
  9. customthe water was decanted
  10. washThe residue was washed with hexane (2×100 mL)
  11. customchromatographed on silica gel eluting with 4:6 ethyl acetate/hexane

Sources & evidence

ORD record
ord-7a68103671a34cf2939af68817bea2fc
Source dataset
uspto-grants-1997_05
Patent number
US05631210

Reaction notes

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