Cyclopentanone → HCID 59619822, compound

HRID 445752Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:23])[C:13](=[O:22])[N:14]([C:15]4[C:16]([CH3:21])=[N:17][N:18]([CH3:20])[CH:19]=4)[C:5]=3[C:4]=2[CH:3]=1.[C:24]1(=[O:29])[CH2:28][CH2:27][CH2:26][CH2:25]1>>[CH3:20][N:18]1[CH:19]=[C:15]([N:14]2[C:5]3[C:4]4[CH:3]=[C:2]([C:6]5[CH:7]=[N:8][CH:9]=[C:4]([C:24]6([OH:29])[CH2:28][CH2:27][CH2:26][CH2:25]6)[CH:5]=5)[CH:11]=[CH:10][C:9]=4[N:8]=[CH:7][C:6]=3[N:12]([CH3:23])[C:13]2=[O:22])[C:16]([CH3:21])=[N:17]1

Participants

Reactant 2

HCID 8452Cyclopentanone

HCID 596197398-Bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one2×

Product 1

HCID 59619822HCID 59619822, compound

Procedure

The title compound was synthesized in a similar manner as described for Example 1.1 using 8-bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate A) and cyclopentanone (Fluka, Buchs, Switzerland) to give the title compound as a white solid. (HPLC: tR 2.14 min (Method A); M+H=455 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.99 (s, 1H), 8.71-8.68 (m, 1H), 8.61-8.58 (m, 1H), 8.16-8.11 (m, 2H), 8.01-7.96 (m, 1H), 7.85-7.81 (m, 1H), 7.63-7.59 (m, 1H), 5.05 (s, 1H), 3.90 (s, 3H), 3.58 (s, 3H), 1.98-1.77 (m, 8H), 1.95 (s, 3H))

Workup

customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record: ord-4cd58567d4e44883872b8e84bd7ae826
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476294B2

Reaction notes

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