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

HRID 901282Notes

Reaction equation

HRID 901282 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[S: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[S:24][CH:25]=[CH:26][CH:27]=2)=[O:22])[CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 6259Phenacyl bromideHCID 692162166-Fluoro-2-oxo-4-[4-(thiophene-2-carbonyl)-piperazine-1-yl]-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile

Product 1

HCID 596996526-Fluoro-2-oxo-1-(2-oxo-2-phenyl-ethyl)-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile

Procedure

This compound was prepared from 6-fluoro-2-oxo-4-[4-(thiophene-2-carbonyl)-piperazine-1-yl]-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile (98) and 2-bromoacetophenone according to General Procedure B. Yield 293 mg (38%), MP 262° C.; 1H-NMR (DMSO-d6): δ 3.79 (m, 4H), 3.95 (m, 4H), 5.87 (s, 2H), 7.16 (dd, J=3.6, 5.2 Hz, 1H), 7.51 (d, J=3.6 Hz, 1H), 7.59 (m, 2H), 7.50 (m, 1H), 7.81 (dd, J=1.2, 4.8 Hz, 1H), 8.12 (m, 2H), 8.23 (dd, J=2.8, 9.2 Hz, 1H), 8.70 (d, J=2.8 Hz, 1H); EIMS: 502 (M+1). Anal. (C26H20FN5O3S) C, H, N.

Sources & evidence

ORD record
ord-a3e21c15e9df4b9eb3b7a333a1135513
Source dataset
uspto-grants-2008_04
Patent number
US07361760B2

Reaction notes

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