Hydrochloric Acid → 2-(Aminomethyl)-4-(4-methoxyphenyl)-5-(3-pyridyl)-1,3-thiazole

HRID 65035Notes

Reaction equation

C(OC([NH:11][CH2:12][C:13]1[S:14][C:15]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[N:17]=1)=O)C1C=CC=CC=1.Cl>O1CCCC1>[NH2:11][CH2:12][C:13]1[S:14][C:15]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[C:16]([C:18]2[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)[N:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

In 10 ml of tetrahydrofuran was dissolved 1.2 g of 2-(benzyloxycarbonylaminomethyl)-4-(4-methoxyphenyl)-5-(3-pyridyl)-1,3-thiazole obtained by Example 11. To the solution was added 10 ml of 5N-HCl, and the mixture was stirred for 2 hours at 80° C. Tetrahydrofuran was evaporated off under reduced pressure. The remaining aqueous layer was made alkaline with 2N-NaOH, which was subjected to extraction with ethyl acetate. The extract was washed with water and dried, then the solvent was evaporated off. The residue was purified by means of a silica-gel column chromatography [eluent: chloroform-methanol (9:1)] to give 0.5 g (yield 60%) of 2-(aminomethyl)-4-(4-methoxyphenyl)-5-(3-pyridyl)-1,3-thiazole.

Workup

customTetrahydrofuran was evaporated off under reduced pressure
extractionwas subjected to extraction with ethyl acetate
washThe extract was washed with water
customdried
customthe solvent was evaporated off
customThe residue was purified by means of a silica-gel column chromatography [eluent: chloroform-methanol (9:1)]

Sources & evidence

ORD record: ord-89c5bdecdcb54726a065aa2ba0eced3e
Source dataset: uspto-grants-1986_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04612321

Reaction notes

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