Dabco → HCID 59699584, compound

HRID 901296Notes

Reaction equation

HRID 901296 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][N:20]=[CH:19][CH: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>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][N:20]=[CH:19][CH:18]=2)=[O:13])[CH3:10]

Participants

5

Reactant 3

HCID 9237DabcoHCID 7975621-(Thien-2-ylcarbonyl)piperazineHCID 59699624HCID 59699624, compound

Product 1

HCID 59699584HCID 59699584, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

DABCO (0.7 g, 6.3 mmol) was added to a solution of 4-chloro-2-oxo-1,2-dihydro-[1,6]-naphthyridine-3-carboxylic acid ethyl ester (120) (0.8 g, 3.16 mmol) and piperazine-1-yl-thiophene-2-yl-methanone (0.93 g, 4.74 mmol) DMA at room temperature. The solution was heated at 110° C. for 2 h. The solution was cooled and poured into ice cold 10% ammonium chloride solution in water. The solids formed were filtered, washed by water, and dried to yield 1.2 g (92%) of 2-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-[1,6]-naphthyridin-3-carboxylic acid ethyl ester (121) as white solids. MP: 231° C.; 1H-NMR (DMSO-d6): δ 1.28 (t, J=7.2 Hz, 3H), 3.18 (m, 4H), 3.89 (m, 4H), 4.27 (q, J=7.2 Hz, 2H), 7.14 (dd, J=3.6, 4.8 Hz, 1H), 7.18 (d, J=6.0 Hz, 1H), 7.47 (d, J=3.6 Hz, 1H), 7.80 (d, J=4.8 Hz, 1H), 8.51 (d, J=5.6 Hz, 1H), 8.91 (s, 1H); EIMS m/z 413 (M+1).

Workup

  1. temperatureThe solution was cooled
  2. customThe solids formed
  3. filtrationwere filtered
  4. washwashed by water
  5. customdried

Sources & evidence

ORD record
ord-4f6ab269f4f6475a8adf00e47aee52cc
Source dataset
uspto-grants-2008_04
Patent number
US07361760B2

Reaction notes

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