Phenacyl bromide → HCID 59699621, compound

HRID 901299Notes

Reaction equation

HRID 901299 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:29])[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][N:12]=[CH:11][CH:10]=2)=[O:5])[CH3:2].Br[CH2:31][C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:33]>>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:29])[N:8]([CH2:31][C:32](=[O:33])[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=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][N:12]=[CH:11][CH:10]=2)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 6259Phenacyl bromideHCID 59699584HCID 59699584, compound

Product 1

HCID 59699621HCID 59699621, compound

Procedure

This compound was prepared from 2-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-[1,6]-naphthyridin-3-carboxylic acid ethyl ester (121) and 2-bromoacetophenone according to General Procedure B. Yield 127 mg (24%), MP 157° C.; 1H-NMR (DMSO-d6): δ 1.27 (t, J=6.8 Hz, 3H), 3.24 (m, 4H), 3.93 (m, 4H), 4.26 (q, J=7.2 Hz, 2H), 5.85 (s, 2H), 7.15 (dd, J=3.6, 5.2 Hz, 1H), 7.47 (m, 2H), 7.62 (m, 2H), 7.74 (m, 1H), 7.80 (d, J=5.2 Hz, 1H), 8.13 (d, J=5.2 Hz, 1H), 8.32 (d, J=7.2 Hz, 2H), 8.56 (d, J=6.0 Hz, 1H), 9.12 (s, 1H); EIMS: 531 (M+1). Anal. (C28H26N4O5S) C, H, N.

Sources & evidence

ORD record
ord-3513c69b94a94052a5d90a3d3d94da8b
Source dataset
uspto-grants-2008_04
Patent number
US07361760B2

Reaction notes

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