Dabco → HCID 11165828, compound

HRID 901240Notes

Reaction equation

C1N2CCN(CC2)C1.[CH2:9]([O:11][C:12]([C:14]1[C:15](=[O:25])[NH:16][C:17]2[C:22]([C:23]=1Cl)=[CH:21][CH:20]=[CH:19][N:18]=2)=[O:13])[CH3:10].[N:26]1([C:32]([C:34]2[S:35][CH:36]=[CH:37][CH:38]=2)=[O:33])[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>CC(N(C)C)=O>[CH2:9]([O:11][C:12]([C:14]1[C:15](=[O:25])[NH:16][C:17]2[C:22]([C:23]=1[N:29]1[CH2:30][CH2:31][N:26]([C:32]([C:34]3[S:35][CH:36]=[CH:37][CH:38]=3)=[O:33])[CH2:27][CH2:28]1)=[CH:21][CH:20]=[CH:19][N:18]=2)=[O:13])[CH3:10]

Participants

Conditions

Temperature: 110 °C

Procedure

DABCO (0.57 g, 5.14 mmol) was added to a solution of 4-chloro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (15) (0.65 g, 2.57 mmol) and piperazine-1-yl-thiophene-2-yl-methanone (0.60 g, 3.08 mmol) in dimethylacetamide at room temperature. The solution was heated overnight at 110° C. The solution was cooled and poured into ice water. The solids formed were filtered, washed by water, and dried to yield 420 mg (39%) of 2-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (16) as white solids. MP: 239° C.; 1H-NMR (DMSO-d6): δ 1.30 (t, J=7.0 Hz, 3H), 3.13 (m, 4H), 3.87 (m, 4H), 4.30 (q, J=7.0 Hz, 2H), 7.15 (dd, J=3.5, 4.8 Hz, 1H), 7.40 (dd, J=4.8, 8.0 Hz, 1H), 7.45 (d, J=3.6 Hz, 1H), 7.80 (d, J=4.8 Hz, 1H), 8.24 (dd, J=1.5, 7.5 Hz, 1H), 8.56 (dd, J=1.5, 7.5 Hz, 1H) 12.25 (s, 1H); EIMS: 413 (M+1).

Workup

temperatureThe solution was cooled
customThe solids formed
filtrationwere filtered
washwashed by water
customdried

Sources & evidence

ORD record: ord-ec016ac32495448e9ab515a4c1fae458
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07361760B2

Reaction notes

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