Triethylamine → HCID 21849009, compound

HRID 617705Notes

Reaction equation

HRID 617705 reaction equation
[CH3:1][C:2]1[C:7]2[C:8]3([CH2:13][CH2:14][S:15](=[O:17])(=[O:16])[C:6]=2[C:5]([CH3:18])=[CH:4][C:3]=1[C:19]([OH:21])=[O:20])[O:12][CH2:11][CH2:10][O:9]3.C(Cl)(=O)C(Cl)=O.[CH2:28]([N:30]1[C:34](O)=[CH:33][CH:32]=[N:31]1)[CH3:29].C(N(CC)CC)C>CN(C)C=O.C(Cl)Cl>[CH3:1][C:2]1[C:7]2[C:8]3([CH2:13][CH2:14][S:15](=[O:17])(=[O:16])[C:6]=2[C:5]([CH3:18])=[CH:4][C:3]=1[C:19]([O:21][C:34]1[N:30]([CH2:28][CH3:29])[N:31]=[CH:32][CH:33]=1)=[O:20])[O:9][CH2:10][CH2:11][O:12]3

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 23532950HCID 23532950, compoundHCID 178418331HCID 178418331, compound

Product 1

HCID 21849009HCID 21849009, compoundYield 15.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1.18 g (3.8 mmol) of the title compound of Step F, 0.99 mL (0.011 mol) of oxalyl chloride (purchased from Janssen), and 2 drops of N,N-dimethylformamide were added to 50 mL of methylene chloride. 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 the resulting mixture was evaporated to dryness. Another 50 mL of methylene chloride was added to the residue, and the solution was cooled to about 0° C. 0.51 g (4.5 mmol) of 1-ethyl-1H-pyrazol-5-ol was added followed by 1.63 mL (0.012 mol) of triethylamine, and the mixture was stirred overnight while warming to room temperature. The mixture was evaporated to dryness and the crude product was chromatographed eluting with a mixture of ethyl acetate:hexane (6:4) to yield 0.24 g of the title compound of Step G as a semi-solid. 1H NMR (CDCl3): δ1.4 (t,3H), 2.5 (s,3H), 2.6 (m,2H), 2.8 (s,3H), 3.5 (m,2H), 4.1-4.4 (m,6H), 6.26 (s,1H), 7.5-7.7 (2H).

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. customthe resulting mixture was evaporated 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. customthe crude product was chromatographed
  9. washeluting with a mixture of ethyl acetate:hexane (6:4)

Sources & evidence

ORD record
ord-7ecf721459204f65a4db0573ffb9a56a
Source dataset
uspto-grants-1999_09
Patent number
US05952266

Reaction notes

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