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

HRID 901278Notes

Reaction equation

HRID 901278 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].[N:16]1([C:22]([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)=[O:23])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>>[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:19]1[CH2:20][CH2:21][N:16]([C:22]([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)=[O:23])[CH2:17][CH2:18]1

Participants

3

Reactant 2

HCID 7975621-(Thien-2-ylcarbonyl)piperazineHCID 692174464,6-Dichloro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile

Product 1

HCID 692183766-Chloro-2-oxo-4-[4-(thiophene-2-carbonyl)-piperazine-1-yl]-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrileYield 74%

Procedure

This compound was prepared from 4,6-dichloro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile (97) and piperazin-1-yl-thiophene-2-yl-methanone according to general procedure E to yield 6.8 g (74%) of 6-chloro-2-oxo-4-[4-(thiophene-2-carbonyl)-piperazine-1-yl]-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile (100) as yellow solids. MP 158° C.; 1H-NMR (DMSO-d6): δ 3.64 (m, 4H), 3.90 (m, 4H), 7.16 (dd, J=3.6, 4.8 Hz, 1H), 7.49 (dd, J=1.2, 3.6 Hz, 1H), 7.81 (dd, J=1.2, 5.2 Hz, 1H), 8.21 (d, J=2.4 Hz, 1H), 8.66 (d, J=2.4 Hz, 1H); EIMS: 400 (M+1).

Sources & evidence

ORD record
ord-8e799cfc0a054b88abc7c06e25b7d231
Source dataset
uspto-grants-2008_04
Patent number
US07361760B2

Reaction notes

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