1-(2-Furoyl)piperazine → 6-Chloro-2-oxo-4-[4-(furan-2-carbonyl)-piperazine-1-yl]-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile

HRID 901279Notes

Reaction equation

HRID 901279 reaction equation
Cl[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[NH:5][C:4](=[O:13])[C:3]=1[C:14]#[N:15].[O:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[C:21]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)=[O:22]>>[Cl:12][C:9]1[CH:10]=[C:11]2[C:6](=[N:7][CH:8]=1)[NH:5][C:4](=[O:13])[C:3]([C:14]#[N:15])=[C:2]2[N:26]1[CH2:27][CH2:28][N:23]([C:21]([C:17]2[O:16][CH:20]=[CH:19][CH:18]=2)=[O:22])[CH2:24][CH2:25]1

Participants

3

Reactant 2

HCID 5502061-(2-Furoyl)piperazineHCID 692174464,6-Dichloro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile

Product 1

HCID 692157666-Chloro-2-oxo-4-[4-(furan-2-carbonyl)-piperazine-1-yl]-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrileYield 71%

Procedure

This compound was prepared from 4,6-dichloro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile (97) and 2-furoyl piperazine according to general procedure E to yield 2.27 g (71%) of 6-chloro-2-oxo-4-[4-(furan-2-carbonyl)-piperazine-1-yl]-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile (101) as yellow solids. MP 303° C.; 1H-NMR (DMSO-d6): δ 3.76 (m, 4H), 3.93 (m, 4H), 6.65 (dd, J=1.6, 3.6 Hz, 1H), 7.09 (d, J=3.6 Hz, 1H), 7.89 (d, J=1.6 Hz, 1H), 8.21 (d, J=2.4 Hz, 1H), 8.66 (d, J=2.4 Hz, 1H), 12.36 (s, 1H); EIMS: 384 (M+1).

Sources & evidence

ORD record
ord-dc887442e8a4492d8981b9958b033be5
Source dataset
uspto-grants-2008_04
Patent number
US07361760B2

Reaction notes

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