Dabco → HCID 59699591, compound

HRID 901300Notes

Reaction equation

HRID 901300 reaction equation
C1N2CCN(CC2)C1.[CH2:9]([N:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][N:24]=2)[C:19](Cl)=[C:18]([N+:27]([O-:29])=[O:28])[C:17]1=[O:30])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[N:31]1([C:37]([C:39]2[S:40][CH:41]=[CH:42][CH:43]=2)=[O:38])[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1>CN1CCCC1=O.O>[CH2:9]([N:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][N:24]=2)[C:19]([N:34]2[CH2:35][CH2:36][N:31]([C:37]([C:39]3[S:40][CH:41]=[CH:42][CH:43]=3)=[O:38])[CH2:32][CH2:33]2)=[C:18]([N+:27]([O-:29])=[O:28])[C:17]1=[O:30])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 9237DabcoHCID 7975621-(Thien-2-ylcarbonyl)piperazineHCID 59699566HCID 59699566, compound

Product 1

HCID 59699591HCID 59699591, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

DABCO (6.26 g, 55 mmol) was added to a solution of 1-benzyl-4-chloro-3-nitro-1,8-naphthyridin-2(1H)-one (126) (8.81 g, 28 mmol) and piperazine-1-yl-thiophene-2-yl-methanone (6.57 g, 33 mmol) in N-methylpyrrolidone 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 yellow solid. Yield 11 g (83%), mp 255° C. 1H-NMR (DMSO-d6): δ 3.26 (m, 4H), 3.90 (m, 4H), 5.61 (s, 2H), 7.15 (m, 1H), 7.25 (m, 5H), 7.47 (m, 2H), 7.80 (d, J=5.2 Hz, 1H), 8.43 (d, J=7.6 Hz, 1H), 8.76 (d, J=4.4 Hz, 1H); EIMS m/z 476 (M+1).

Workup

  1. temperatureThe solution was cooled
  2. customThe solids formed
  3. filtrationwere filtered
  4. washwashed by water
  5. customdried
  6. customto yield yellow solid

Sources & evidence

ORD record
ord-59fb9503150b4df18deb8721a287c297
Source dataset
uspto-grants-2008_04
Patent number
US07361760B2

Reaction notes

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