Methyl 4-(bromomethyl)benzoate → HCID 11852700, compound

HRID 902513Notes

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].[CH3:29][O:30][C:31](=[O:40])[C:32]1[CH:37]=[CH:36][C:35]([CH2:38]Br)=[CH:34][CH:33]=1>>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:28])[N:8]([CH2:38][C:35]2[CH:34]=[CH:33][C:32]([C:31]([O:30][CH3:29])=[O:40])=[CH:37][CH:36]=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 256687Methyl 4-(bromomethyl)benzoate

HCID 59702104HCID 59702104, compound

Product 1

HCID 11852700HCID 11852700, compoundYield 51%

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 methyl-4-bromomethylbenzoate by applying general procedure A. Yield 51%; 1H NMR (400 MHz, DMSO-d6) δ 1.25 (t, J=7.2 Hz, 3H), 3.30 (m, 4H), 3.82 (m, 7H), 4.27 (q, J=7.2 Hz, 2H), 5.28 (s, 2H), 7.12 (d, J=3.2 Hz, 1H), 7.16 (dd, J=5.2, 3.2 Hz, 1H), 7.37 (m, 2H), 7.47 (dd, J=1.2, 3.6 Hz, 1H), 7.79 (dd, J=1.2, 5.2 Hz, 1H), 7.91 (m, 2H), 8.13 (d, J=3.2 Hz, 1H) ppm; MS m/z=565 amu (M++1). Anal. (C28H27N3O6S2) C, H, N.

Sources & evidence

ORD record: ord-50b3f8353581428dbcca98f62e2f520c
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07365200B2

Reaction notes

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