Diisopropylethylamine → 2-Amino-5-[(3-carbomethoxyphenyl)thio]thiazole

HRID 968197Notes

Reaction equation

C(OC([NH:8][C:9]1[S:10][C:11]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([OH:23])=[O:22])[CH:16]=2)=[CH:12][N:13]=1)=O)(C)(C)C.[C:24](N1CCNCC1)(=O)C.ON1C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>C1COCC1>[CH3:24][O:23][C:21](=[O:22])[C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([S:14][C:11]2[S:10][C:9]([NH2:8])=[N:13][CH:12]=2)[CH:16]=1

Participants

Conditions

Temperature: 55 °C

Procedure

A suspension of 2-tert-butoxycarbonylamino-5-[(3-carboxyphenyl)thio]thiazole (528 mg, 1.5 mmol), N-acetylpiperazine (239 mg, 1.87 mmol), ethyl-3-(3-dimethylamino)propyl carbodiimide hydrochloride (400 mg, 2 mmol), 1-hydroxy-7-azabenzotriazole (272 mg, 2 mmol) and diisopropylethylamine (560 μL, 4 mmol) in THF (20 mL) was heated to 55° C. for 2 h. The mixture was cooled to rt. and concentrated. The residue was purified using column chromatography on silica gel eluted with 2% methanol in dichloromethane followed by 5% methanol in dichloromethane to obtain the titled compound (400 mg, 58%) as a white foam. E. 4-Acetyl-1-[3-[(2-aminothiazol-5-yl)thio]benzoyl]piperazine

Workup

temperatureThe mixture was cooled to rt
concentrationand concentrated
customThe residue was purified
washeluted with 2% methanol in dichloromethane

Sources & evidence

ORD record: ord-91836e50768442dd81257eedc01a7dac
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06958336B2

Reaction notes

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