Phenacyl bromide → HCID 11852797, compound

HRID 902511Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:28])[NH:8][C:9]2[C:13]([C:14]=1[N:15]1[CH2:20][CH2:19][N:18]([C:21]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=[O:22])[CH2:17][CH2:16]1)=[CH:12][S:11][CH:10]=2)=[O:5])[CH3:2].Br[CH2:30][C:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:32]>>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:28])[N:8]([CH2:30][C:31](=[O:32])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:9]2[C:13]([C:14]=1[N:15]1[CH2:16][CH2:17][N:18]([C:21]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=[O:22])[CH2:19][CH2:20]1)=[CH:12][S:11][CH:10]=2)=[O:5])[CH3:2]

Participants

Reactant 2

HCID 6259Phenacyl bromide

HCID 59702104HCID 59702104, compound

Product 1

HCID 11852797HCID 11852797, compoundYield 66%

Procedure

The compound was prepared from 5-oxo-7-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-4,5-dihydro-2-thia-4-aza-indene-6-carboxylic acid ethyl ester (40) and 2-bromoacetophenone by applying general procedure A. Yield 66%; 1H NMR (400 MHz, DMSO-d6) δ 1.25 (t, J=7.2 Hz, 3H), 3.34 (m, 4H), 3.86 (m, 4H), 4.24 (q, J=7.2 Hz, 2H), 5.58 (s, 2H), 7.15 (dd, J=3.6, 4.6 Hz, 1H), 7.24 (d, J=3.2 Hz, 1H), 7.48 (dd, J=1.2, 3.6 Hz, 1H), 7.60 (m, 2H), 7.71 (m, 1H), 7.80 (dd, J=1.2, 4.8 Hz, 1H), 8.09 (m, 2H), 8.16 (d, J=3.2 Hz, 1H) ppm; MS m/z=535 amu (M++1). Anal. (C27H25N3O5S2) C, H, N.

Sources & evidence

ORD record: ord-b89a43b4317a46678edfe4a2d4954d00
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07365200B2

Reaction notes

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