1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 19006043, compound

HRID 1742985Notes

Reaction equation

Cl.[N:2]1([CH:7]2[CH2:11][CH2:10][NH:9][CH2:8]2)[CH:6]=[CH:5][N:4]=[N:3]1.C1CCN2C(=NCCC2)CC1.[NH2:23][C:24]1[C:33]([F:34])=[C:32](F)[C:31]([O:36][CH3:37])=[C:30]2[C:25]=1[C:26](=[O:44])[C:27]([C:41]([OH:43])=[O:42])=[CH:28][N:29]2[CH:38]1[CH2:40][CH2:39]1>N1C=CC=CC=1>[NH2:23][C:24]1[C:33]([F:34])=[C:32]([N:9]2[CH2:10][CH2:11][CH:7]([N:2]3[CH:6]=[CH:5][N:4]=[N:3]3)[CH2:8]2)[C:31]([O:36][CH3:37])=[C:30]2[C:25]=1[C:26](=[O:44])[C:27]([C:41]([OH:43])=[O:42])=[CH:28][N:29]2[CH:38]1[CH2:40][CH2:39]1

Participants

Conditions

Temperature: 120 °C

Procedure

3-(1,2,3-triazol-1-yl)pyrrolidinehydrochloride (147 mg, 0.84 mmol) and DBU (128 mg, 0.84 mmol) were added to a suspension of 5-Amino-1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (100 mg, 0.33 mmol) in pyridine (5 ml). The reaction mixture was heated at 120° C. for 30 hrs, concentrated and the residue was triturated with water. The separated solid was filtered, washed with water and recrystallized from chloroform-hexane. Yield 40 mg; m.p. 208° C.; 1H NMR (TFA) δ: 9.39 (s, 1H), 8.70 (s, 1H), 8.57 (s, 1H), 5.88 (s, 1H), 4.43-4.73 (m, 4H), 4.10 (m, 1H), 3.79 (s, 3H), 2.92 (m, 2H), 1.12-1.58 (m, 4H).

Workup

concentrationconcentrated
customthe residue was triturated with water
filtrationThe separated solid was filtered
washwashed with water
customrecrystallized from chloroform-hexane

Sources & evidence

ORD record: ord-7cee625a748944498f5aad783c6ffe72
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05342846

Reaction notes

Loading…