Dabco → HCID 59699675, compound

HRID 901293Notes

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]([S:27]([CH3:30])(=[O:29])=[O:28])[C:17]1=[O:31])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[N:32]1([C:38]([C:40]2[S:41][CH:42]=[CH:43][CH:44]=2)=[O:39])[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]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:35]2[CH2:36][CH2:37][N:32]([C:38]([C:40]3[S:41][CH:42]=[CH:43][CH:44]=3)=[O:39])[CH2:33][CH2:34]2)=[C:18]([S:27]([CH3:30])(=[O:29])=[O:28])[C:17]1=[O:31])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 110 °C

Procedure

DABCO (0.57 g, 5.0 mmol) was added to a solution of 1-benzyl-4-chloro-3-(methylsulfonyl)-[1,8]-naphthyridin-2(1H)-one (115) (0.88 g, 2.5 mmol) and piperazine-1-yl-thiophene-2-yl-methanone (0.60 g, 3.08 mmol) in N-methylpyrrolidone at room temperature. The solution was heated at 110° C. for 15 min. 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 0.95 g (74%) of 1-benzyl-3-methanesulfonyl-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1H-[1,8]-naphthyridin-2-one (116) as yellow solids MP: 223° C.; 1H-NMR (DMSO-d6): δ 3.37 (s, 3H), 3.59 (m, 4H), 3.93 (b, 4H), 5.59 (s, 2H), 7.2 (m, 6H), 7.38 (m, 1H), 7.47 (dd, J=1.2, 3.6 Hz, 1H), 7.81 (dd, J=1.2, 5.2 Hz, 1H), 8.46 (dd, J=1.6, 8.0 Hz, 1H), 8.70 (dd, J=1.6, 4.4 Hz, 1H); EIMS m/z 509 (M+1).

Workup

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

Sources & evidence

ORD record: ord-88b031bec8bf4012b4b03560003ccc27
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07361760B2

Reaction notes

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