1,8-Diazabicyclo(5.4.0)undec-7-ene → Ethyl 1-cyclopropyl-6-fluoro-7-[4-(1,2,3-triazol-1-yl)piperidin-1-yl]-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

HRID 1742980

Reaction equation

Cl.[N:2]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][N:4]=[N:3]1.C1CCN2C(=NCCC2)CC1.[CH:24]1([N:27]2[C:36]3[C:31](=[CH:32][C:33]([F:38])=[C:34](Cl)[N:35]=3)[C:30](=[O:39])[C:29]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:28]2)[CH2:26][CH2:25]1>C(#N)C.N1C=CC=CC=1>[CH:24]1([N:27]2[C:36]3[C:31](=[CH:32][C:33]([F:38])=[C:34]([N:10]4[CH2:11][CH2:12][CH:7]([N:2]5[CH:6]=[CH:5][N:4]=[N:3]5)[CH2:8][CH2:9]4)[N:35]=3)[C:30](=[O:39])[C:29]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:28]2)[CH2:25][CH2:26]1

Participants

Conditions

Temperature: 100 °C

Procedure

4-(1,2,3-triazol-1-yl)piperidine hydrochloride (225 mg, 1.2 mmol) and DBU (182 mg, 1.2 mmol) was added to a suspension of ethyl 1-cyclopropyl-6-fluoro-7-chloro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (150 mg, 0.48 mmol) in a mixture of acetonitrile (10 ml) and pyridine (3 ml). The reaction mixture was heated at 100° C. for 5 hrs. The suspended solid was filtered and the filtrate was concentrated to dryness. The residue was triturated with water and separated solid was filtered, washed with water and dried to give 135 mg of desired product. m.p. 213°-214° C.; 1H NMR (CDCl3) δ: 8.48 (s, 1H), 8.11 (d, 1H), 7.72 (s, 1H), 7.60 (s, 1H), 4.60-4.85 (m, 3H), 4.29-4.40 (q, 2H), 3.43-3.54 (m, 1H), 3.21-3.35 (m, 2H), 2.10-2.36 (m, 4H), 1.36 (t, 3H), 0.95-1.23 (m, 4H).

Workup

filtrationThe suspended solid was filtered
concentrationthe filtrate was concentrated to dryness
customThe residue was triturated with water
customseparated solid
filtrationwas filtered
washwashed with water
customdried

Sources & evidence

ORD record: ord-11c49ca4866945bca119484875332fd1
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05342846

Linked notes

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