2-Oxopropanethioamide → 5'-Bromo-4-methoxy-5''-methyldispiro[cyclohexane-1,2'-[1]-benzofuran-3',2''-imidazole]-4''(3''H)-thione

HRID 1770959Notes

Reaction equation

HRID 1770959 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:16][C:8]3([CH2:13][CH2:12][CH:11]([O:14][CH3:15])[CH2:10][CH2:9]3)[C:7](=[NH:17])[C:6]=2[CH:18]=1.O=[C:20]([CH3:24])[C:21](=[S:23])[NH2:22]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:16][C:8]3([CH2:9][CH2:10][CH:11]([O:14][CH3:15])[CH2:12][CH2:13]3)[C:7]3([NH:22][C:21](=[S:23])[C:20]([CH3:24])=[N:17]3)[C:6]=2[CH:18]=1

Participants

4

Reactant 2

HCID 207652372-Oxopropanethioamide3×HCID 679795445-Bromo-4'-methoxy-3H-spiro[benzofuran-2,1'-cyclohexan]-3-imine

Product 1

HCID 866672755'-Bromo-4-methoxy-5''-methyldispiro[cyclohexane-1,2'-[1]-benzofuran-3',2''-imidazole]-4''(3''H)-thioneYield 21.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

5-Bromo-4′-methoxy-3H-spiro[benzofuran-2,1′-cyclohexan]-3-imine (Example 29 Step 2, 1.37 g, 4.41 mmol) and 2-oxopropanethioamide (Intermediate 2, 0.909 g, 8.81 mmol) were dissolved in dry MeOH (25 mL) and the resulting orange solution was heated at 60° C. under a nitrogen atmosphere overnight. More 2-oxopropanethioamide (400 mg) was added and stirring continued. After 24 h the mixture was allowed to cool to r.t. and the solvent was evaporated. Purification by flash chromatography using a gradient of 0-100% EtOAc in heptane afforded 373 mg of the title compound (21% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.35 (m, 1H), 1.47 (m, 3H), 1.87 (m, 2H), 1.97 (m, 2H), 2.29 (s, 3H), 3.13 (s, 3H), 4.11 (m, 1H), 6.99 (d, 1H), 7.16 (d, 1H), 7.48 (dd, 1H); MS (ES+) m/z 396 [M+H]+.

Workup

  1. temperatureto cool to r.t.
  2. customthe solvent was evaporated
  3. customPurification by flash chromatography

Sources & evidence

ORD record
ord-342739e38bcd4ea588347cea09121623
Source dataset
uspto-grants-2016_02
Patent number
US09248129B2

Reaction notes

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