Hydrochloric Acid → HCID 20145006, compound

HRID 1906008Notes

Reaction equation

[CH3:1][NH:2][C:3]1[S:4][C:5]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[C:6]([C:8]([O:10]CC)=O)[N:7]=1.[NH2:19][CH2:20][CH:21]1[CH2:25][CH2:24][CH2:23][N:22]1[CH2:26][CH3:27].Cl.O>C(O)CO>[CH3:1][NH:2][C:3]1[S:4][C:5]([C:13]2[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=2)=[C:6]([C:8](=[O:10])[NH:19][CH2:20][CH:21]2[CH2:25][CH2:24][CH2:23][N:22]2[CH2:26][CH3:27])[N:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of ethyl 2-methylamino-5-(4-pyridyl)-4-thiazolecarboxylate (2.63 g), 2-aminomethyl-1-ethylpyrrolidine (2.6 g) in a mixture of ethyleneglycol (10 ml) and conc. HCl (0.5 ml) was stirred at 80° C. for 6 hours. The reaction mixture was poured into water and the resultant solution was extracted with ethyl acetate. The organic extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was subjected to column chromatography on alumina eluting with a mixture of diisopropylether and ethylacetate (1:1) and the fractions containing the desired compound were combined and evaporated in vacuo to give 2-methylamino-5-(4-pyridyl)-4-[(1-ethyl-2-pyrrolidinyl)methylcarbamoyl]thiazole (1.5 g). mp 76°-8° C.

Workup

extractionthe resultant solution was extracted with ethyl acetate
extractionThe organic extract
washwas washed with brine
dry with materialdried over magnesium sulfate
customThe solvent was evaporated in vacuo
additionthe residue was subjected to column chromatography on alumina eluting with a mixture of diisopropylether and ethylacetate (1:1)
additionthe fractions containing the desired compound
customevaporated in vacuo

Sources & evidence

ORD record: ord-c5fe74de1649429388231c5fec2acb6e
Source dataset: uspto-grants-1987_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04649146

Reaction notes

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