Dabco → HCID 59699558, compound

HRID 901244Notes

Reaction equation

HRID 901244 reaction equation
N12CCN(CC1)CC2.Cl[C:10]1[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[NH:13][C:12](=[O:20])[C:11]=1[C:21]#[N:22].[N:23]1([C:29]([C:31]2[S:32][CH:33]=[CH:34][CH:35]=2)=[O:30])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>CC(N(C)C)=O>[O:20]=[C:12]1[C:11]([C:21]#[N:22])=[C:10]([N:26]2[CH2:27][CH2:28][N:23]([C:29]([C:31]3[S:32][CH:33]=[CH:34][CH:35]=3)=[O:30])[CH2:24][CH2:25]2)[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[NH:13]1

Participants

5

Reactant 3

HCID 9237DabcoHCID 7975621-(Thien-2-ylcarbonyl)piperazineHCID 59699556HCID 59699556, compound

Product 1

HCID 59699558HCID 59699558, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

1,4-Diazabicyclo[2.2.2]-octane (8.60 g, 77 mmol) was added to a solution of 4-chloro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile (31) (7.9 g, 38 mmol) and piperazin-1-yl-thiophene-2-yl-methanone (11.30 g, 57 mmol) in dimethylacetamide at room temperature. The solution was heated at 110° C. overnight. The solution was cooled and poured into ice cold 10% NH4Cl solution. The solids formed were filtered, washed by cold water and dried under vacuum at room temperature to yield 7.1 g (51%) of 2-oxo-4-[4-(thiophene-2-carbonyl)-piperazine-1-yl]-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile (33) as white solids. MP 320° C.; 1H-NMR (DMSO-d6): δ 3.69 (m, 4H), 3.90 (m, 4H), 7.16 (dd, J=3.6, 4.8 Hz, 1H), 7.30 (dd, J=4.4, 8.0 Hz, 1H), 7.49 (d, J=3.6 Hz, 1H), 7.80 (d, J=4.8 Hz, 1H), 8.20 (dd, J=2.0, 8.0 Hz, 1H), 8.60 (d, J=3.2 Hz, 1H), 12.20 (S, 1H); EIMS: 366 (M+1).

Workup

  1. temperatureThe solution was cooled
  2. customThe solids formed
  3. filtrationwere filtered
  4. washwashed by cold water
  5. customdried under vacuum at room temperature

Sources & evidence

ORD record
ord-239a2e4c50ed41d785df54c9e42aa6a3
Source dataset
uspto-grants-2008_04
Patent number
US07361760B2

Reaction notes

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