Triethylamine → ethyl 1-[(4-{3-[(methoxyacetyl)amino]phenyl}-1,3-thiazol-2-yl)methyl]-1H-pyrazole-4-carboxylate

HRID 1257336Notes

Reaction equation

HRID 1257336 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([CH2:13][N:14]3[CH:18]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:16]=[N:15]3)[S:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:31][O:32][CH2:33][C:34](Cl)=[O:35]>O1CCCC1>[CH3:31][O:32][CH2:33][C:34]([NH:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([CH2:13][N:14]3[CH:18]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:16]=[N:15]3)[S:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1)=[O:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 58127539HCID 58127539, compound

Product 1

HCID 58127684ethyl 1-[(4-{3-[(methoxyacetyl)amino]phenyl}-1,3-thiazol-2-yl)methyl]-1H-pyrazole-4-carboxylateYield 96.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution (4 mL) of the crude compound (290 mg, 0.88 mmol) obtained in Example 26a in tetrahydrofuran was cooled in an ice bath, triethylamine (0.16 mL, 1.14 mmol) and methoxyacetylchloride (115 mg, 1.06 mmol) were added, and the mixture was stirred at room temperature overnight. After confirmation of the termination of the reaction by TLC, the resulting salt was removed. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=30/70-ethyl acetate) to give the title compound (339 mg, 96% in 2 steps) as a colorless oil.

Workup

  1. customAfter confirmation of the termination of the reaction by TLC
  2. customthe resulting salt was removed
  3. customThe solvent was evaporated under reduced pressure
  4. customThe resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=30/70-ethyl acetate)

Sources & evidence

ORD record
ord-d310712838b644a39bf77c00d23d8bd7
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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