Ammonia → HCID 10790357, compound

HRID 256595Notes

Reaction equation

[Br:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([C:18]([O:20][CH2:21][CH3:22])=[O:19])([CH2:14][C:15]([OH:17])=O)[N:10]3[CH:23]=[CH:24][CH:25]=[C:9]3[C:8]2=[O:26])=[C:4]([F:29])[CH:3]=1.O[N:31]1C(=O)CCC1=O.Cl.C(N=C=NCCCN(C)C)C.N.Cl>ClCCl.C(#N)C>[CH2:21]([O:20][C:18]([C:11]1([CH2:14][C:15](=[O:17])[NH2:31])[N:10]2[CH:23]=[CH:24][CH:25]=[C:9]2[C:8](=[O:26])[N:7]([CH2:6][C:5]2[CH:27]=[CH:28][C:2]([Br:1])=[CH:3][C:4]=2[F:29])[C:12]1=[O:13])=[O:19])[CH3:22]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 2-(4-bromo-2-fluorobenzyl)-4-ethoxycarbonyl-1,3-dioxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-4-acetic acid (21.4 g), N-hydroxysuccinimide (5.8 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (10.5 g) in dichloromethane (150 ml) was stirred at 25° C. for 1 hour, and 7.8% (w/w) ammonia in acetonitrile (40 ml) was added. The resulting mixture was stirred at 25° C. for 1 hour, poured into 5% hydrochloric acid, and extracted with dichloromethane. The extracts were dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate/n-hexane to give the title compound (18.5 g, 86.4%) as colorless crystals, mp 190°-192° C.

Workup

stirringThe resulting mixture was stirred at 25° C. for 1 hour
extractionextracted with dichloromethane
dry with materialThe extracts were dried over anhydrous sodium sulfate
customevaporated under reduced pressure
customThe residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record: ord-d84487f211274a0ebce59b6ce87cdbdb
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05258382

Reaction notes

Loading…