Phenacyl bromide → 6-Fluoro-4-[4-(furan-2-carbonyl)-piperazin-1-yl]-2-oxo-1-(2-oxo-2-phenyl-ethyl)-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile

HRID 901285Notes

Reaction equation

HRID 901285 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([C:13]#[N:14])=[C:5]2[N:15]1[CH2:20][CH2:19][N:18]([C:21]([C:23]2[O:24][CH:25]=[CH:26][CH:27]=2)=[O:22])[CH2:17][CH2:16]1.Br[CH2:29][C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:31]>>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[N:8]([CH2:29][C:30](=[O:31])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:7](=[O:12])[C:6]([C:13]#[N:14])=[C:5]2[N:15]1[CH2:20][CH2:19][N:18]([C:21]([C:23]2[O:24][CH:25]=[CH:26][CH:27]=2)=[O:22])[CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 6259Phenacyl bromideHCID 692157496-Fluoro-2-oxo-4-[4-(furan-2-carbonyl)-piperazine-1-yl]-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile

Product 1

HCID 692172616-Fluoro-4-[4-(furan-2-carbonyl)-piperazin-1-yl]-2-oxo-1-(2-oxo-2-phenyl-ethyl)-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile

Procedure

This compound was prepared from 6-fluoro-2-oxo-4-[4-(furan-2-carbonyl)-piperazine-1-yl]-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile (99) and 2-bromoacetophenone according to General Procedure B. Yield 242 mg (31%), MP 293° C.; 1H-NMR (DMSO-d6): δ 3.79 (m, 4H), 3.98 (m, 4H), 5.87 (s, 2H), 6.67 (dd, J=1.6, 3.2 Hz, 1H), 7.10 (d, J=3.6 Hz, 1H) 7.59 (m, 2H), 7.73 (m, 1H), 7.90 (d, J=1.6 Hz, 1H), 8.12 (m, 2H), 8.21 (dd, J=2.8, 9.2 Hz, 1H), 8.70 (d, J=2.8 Hz, 1H); EIMS: 486 (M+1). Anal. (C26H20FN5O4) C, H, N.

Sources & evidence

ORD record
ord-469c421dd00847bc95dcec727c1eba06
Source dataset
uspto-grants-2008_04
Patent number
US07361760B2

Reaction notes

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