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

HRID 1257364Notes

Reaction equation

HRID 1257364 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.[C:31]([O:34][CH2:35][C:36](Cl)=[O:37])(=[O:33])[CH3:32]>O1CCCC1>[C:31]([O:34][CH2:35][C:36]([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:37])(=[O:33])[CH3:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 58127539HCID 58127539, compound

Product 1

HCID 66939480ethyl 1-{[4-(3-{[(acetyloxy)acetyl]amino}phenyl)-1,3-thiazol-2-yl]methyl}-1H-pyrazole-4-carboxylateYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (4 mL) of the crude compound (310 mg, 0.88 mmol) obtained in Example 26a in tetrahydrofuran were added triethylamine (0.16 mL, 1.1 mmol) and acetoxyacetylchloride (145 mg, 1.1 mmol), 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=7/3) to give the title compound (270 mg, 72% 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=7/3)

Sources & evidence

ORD record
ord-233d28bd2c3f4d05b91b7a8a4e8c49f9
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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