1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86747533, compound

HRID 1198577Notes

Reaction equation

Cl[C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][C:3]=1[F:19].C(OC([NH:27][CH:28]1[CH2:32][CH2:31][NH:30][CH2:29]1)=O)(C)(C)C.N12CCCN=C1CCCCC2>C(#N)C>[NH2:27][CH:28]1[CH2:32][CH2:31][N:30]([C:8]2[N:9]([CH:12]3[CH2:14][CH2:13]3)[C:10]3[C:5]([C:6](=[O:18])[C:7]=2[C:15]([OH:17])=[O:16])=[CH:4][C:3]([F:19])=[CH:2][N:11]=3)[CH2:29]1

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of 5.65 g (20 mmole) of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8 -naphthyridine-3-carboxylic acid, 4.65 g (25 mmole) of 3-t-butoxycarbonylaminopyrrolidine, 7.9 g (50 mmole) of 1,8-diazabicyclo[5.4.0]undec-7-ene and 150 mL of acetonitrile was stirred at 60° C. for one hour. The solvent was removed in vacuo and the residue was dissolved in 100 mL of trifluoroacetic acid. After stirring at room temperature for one hour, the solvent was removed in vacuo and the residue was suspended in water and the pH adjusted to 11.5 with 50% sodium hydroxide. After filtering through a fiberglass pad to clarify, the filtrate was acidified to 6.6 with 6M hydrochloric acid. The resulting precipitate was removed by filtration, washed with water, 2-propanol, ether, and dried in vacuo to give 6.5 g (98%) of the title compound, mp 284°-286° C.

Workup

customThe solvent was removed in vacuo
dissolutionthe residue was dissolved in 100 mL of trifluoroacetic acid
stirringAfter stirring at room temperature for one hour
customthe solvent was removed in vacuo
filtrationAfter filtering through a fiberglass pad
customThe resulting precipitate was removed by filtration
washwashed with water, 2-propanol, ether
customdried in vacuo

Sources & evidence

ORD record: ord-afb8d584c70f45b9ae0c2f4110239883
Source dataset: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05281612

Reaction notes

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