Phenacyl bromide → HCID 59699568, compound

HRID 901269Notes

Reaction equation

HRID 901269 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:30])[NH:8][C:9]2[C:14]([C:15]=1[N:16]1[CH2:21][CH2:20][N:19]([C:22]([C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)=[O:23])[CH2:18][CH2:17]1)=[CH:13][C:12]([Cl:29])=[CH:11][N:10]=2)=[O:5])[CH3:2].Br[CH2:32][C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:34]>>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:30])[N:8]([CH2:32][C:33](=[O:34])[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:9]2[C:14]([C:15]=1[N:16]1[CH2:21][CH2:20][N:19]([C:22]([C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)=[O:23])[CH2:18][CH2:17]1)=[CH:13][C:12]([Cl:29])=[CH:11][N:10]=2)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 6259Phenacyl bromideHCID 69216352HCID 69216352, compound

Product 1

HCID 59699568HCID 59699568, compound

Procedure

This compound was prepared from 6-chloro-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (82) and 2-bromoacetophenone according to General Procedure B. Yield 333 mg (59%), MP 227° C.; 1H-NMR (DMSO-d6): δ 1.29 (t, J=7.2 Hz, 3H), 3.20 (m, 4H), 3.92 (m, 4H), 4.32 (q, J=7.2 Hz, 2H), 5.87 (s, 2H), 7.17 (dd, J=3.6, 4.8 Hz, 1H), 7.48 (dd, J=1.2, 3.6 Hz, 1H), 7.61 (m, 2H), 7.73 (m, 1H), 7.81 (dd, J=1.2, 4.8 Hz, 1H), 8.11 (m, 2H), 8.32 (d, J=2.6 Hz, 1H), 8.64 (d, J=2.8 Hz, 1H); EIMS: 565 (M+1). Anal. (C28H25ClN4O5S) C, H, N.

Sources & evidence

ORD record
ord-4e56b10a542746f48c5f0d238abbaed5
Source dataset
uspto-grants-2008_04
Patent number
US07361760B2

Reaction notes

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