Ethylamine → HCID 178464964, compound

HRID 396394Notes

Reaction equation

HRID 396394 reaction equation
C(O[C:4]([C:6]1[NH:7][N:8]=[C:9]([C:12]2[S:16][C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:14][CH:13]=2)[C:10]=1[Cl:11])=[O:5])C.[CH2:23]([NH2:25])[CH3:24]>O1CCCC1.O>[CH2:23]([NH:25][C:4]([C:6]1[NH:7][N:8]=[C:9]([C:12]2[S:16][C:15]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[N:14][CH:13]=2)[C:10]=1[Cl:11])=[O:5])[CH3:24]

Participants

5

Reactant 2

HCID 6341EthylamineHCID 178470420HCID 178470420, compound

Product 1

HCID 178464964HCID 178464964, compoundYield 33.4%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To 15 mg (0.045 mmol) of the above-prepared 4-chloro-5-(2-phenyl-thiazol-5-yl)-2H-pyrazole-3-carboxylic acid ethyl ester was added 45 mg (1.0 mmol) of 2M ethylamine in tetrahydrofuran followed by the addition of 2 drops of water. The mixture was heated to 60° C. in a sealed tube and allowed to stir overnight. The solvent was evaporated under reduced pressure and the residue was purified by chromatography on silica gel using 2:5 ethyl acetate:hexanes as eluant to give 5 mg of the title compound (33%). 1H NMR (500 MHz, CDCl3) δ 8.39 (s, 1H) 8.00 (d, 2H) 7.47 (m, 3H) 6.78 (m, 1H) 3.58 (m, 2H) 1.32 (t, 3H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by chromatography on silica gel using 2:5 ethyl acetate

Sources & evidence

ORD record
ord-63dbca51764148c98adfcadda1398e75
Source dataset
uspto-grants-2003_08
Patent number
US06608087B1

Reaction notes

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