2-Oxopropanethioamide → 7'-Bromo-4-methoxy-5''-methyl-3',4'-dihydrodispiro[cyclohexane-1,2'-naphthalene-1',2''-imidazole]-4''(3''H)-thione

HRID 1468233Notes

Reaction equation

HRID 1468233 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8]3([CH2:17][CH2:16][CH:15]([O:18][CH3:19])[CH2:14][CH2:13]3)[C:9]2=[NH:12])=[CH:4][CH:3]=1.O=[C:21]([CH3:25])[C:22](=[S:24])[NH2:23]>CO>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8]3([C:9]42[NH:23][C:22](=[S:24])[C:21]([CH3:25])=[N:12]4)[CH2:17][CH2:16][CH:15]([O:18][CH3:19])[CH2:14][CH2:13]3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 207652372-Oxopropanethioamide2×HCID 867067097'-Bromo-4-methoxy-3',4'-dihydro-1'H-spiro[cyclohexane-1,2'-naphthalen]-1'-imine2×

Product 1

HCID 867067107'-Bromo-4-methoxy-5''-methyl-3',4'-dihydrodispiro[cyclohexane-1,2'-naphthalene-1',2''-imidazole]-4''(3''H)-thioneYield 43.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

7′-Bromo-4-methoxy-3′,4′-dihydro-1′H-spiro[cyclohexane-1,2′-naphthalen]-1′-imine (Intermediate 14, 0.350 g, 1.09 mmol) and 2-oxopropanethioamide (Intermediate 1, 0.336 g, 3.26 mmol) were dissolved in dry MeOH (5 mL) and the resulting orange solution was heated at 60° C. under N2 (g) overnight. The mixture was concentrated and purified by flash column chromatography using a gradient of 0-10% EtOAc in heptane to give the title compound (0.192 g, 43% yield): MS (ES+) m/z 407.12 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-201087d91b4241139b27c8aec8d5d189
Source dataset
uspto-grants-2015_04
Patent number
US09000184B2

Reaction notes

Loading…