Diisopropylethylamine → HCID 9914277, compound

HRID 967733Notes

Reaction equation

C(O[C:6]([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)[CH:16]=2)=[CH:12][N:13]=1)=[O:7])(C)(C)C.[C:24]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)(=[O:26])[CH3:25].ON1[C:38]2N=CC=[CH:42][C:37]=2N=N1.[CH:43]([N:46]([CH:49]([CH3:51])[CH3:50])[CH2:47]C)(C)C>C1COCC1>[C:24]([N:27]1[CH2:32][CH2:31][N:30]([C:21]([C:17]2[CH:16]=[C:15]([S:14][C:11]3[S:10][C:9]([NH:8][C:6](=[O:7])[C:37]4[CH:42]=[CH:51][C:49]([N:46]([CH3:47])[CH3:43])=[CH:50][CH:38]=4)=[N:13][CH:12]=3)[CH:20]=[CH:19][CH:18]=2)=[O:23])[CH2:29][CH2:28]1)(=[O:26])[CH3:25]

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-7efff573a0af4d4b80fbb48ad0d6ee36
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06956045B2

Reaction notes

Loading…