2-Oxopropanethioamide → 6'-Bromo-5-methyl-2'',3'',5'',6''-tetrahydro-3'H-dispiro[imidazole-2,1'-indene-2',4''-pyran]-4(3H)-thione

HRID 1770945Notes

Reaction equation

HRID 1770945 reaction equation
[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([CH2:6][C:7]3([C:13]2=[NH:16])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]3)=[CH:4][CH:3]=1.O=[C:18]([CH3:22])[C:19](=[S:21])[NH2:20]>CO>[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([CH2:6][C:7]3([C:13]42[NH:20][C:19](=[S:21])[C:18]([CH3:22])=[N:16]4)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 207652372-Oxopropanethioamide2×HCID 679795066-Bromo-2',3',5',6'-tetrahydrospiro[indene-2,4'-pyran]-1(3H)-imine

Product 1

HCID 866672736'-Bromo-5-methyl-2'',3'',5'',6''-tetrahydro-3'H-dispiro[imidazole-2,1'-indene-2',4''-pyran]-4(3H)-thioneYield 125.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

6-Bromo-2′,3′,5′,6′-tetrahydrospiro[indene-2,4′-pyran]-1(3H)-imine (Example 25 Step 2, 235 mg, 0.84 mmol) and 2-oxopropanethioamide (Intermediate 2, 173 mg, 1.68 mmol) were taken up in anhydrous MeOH (5 mL) and the resulting mixture was stirred at 60° C. under a nitrogen atmosphere for 3 h. When cooled to r.t. the mixture was concentrated and purified on a silica gel column eluted with 0-50% EtOAc in heptane to give 385 mg (95% yield) of the title compound; 1H NMR (500 MHz, DMSO-d6) δ ppm 12.40 (br. s, 1H), 7.53 (dd, 1H), 7.36 (d, 1H), 7.03 (d, 1H), 3.71 (td, 2H), 3.44 (m, 2H), 3.15 (m, 2H), 2.29 (s, 3H), 1.64 (s, 1H), 1.55 (s, 1H), 1.27 (m, 2H); MS (ES+) m/z 365 [M+H]

Workup

  1. temperatureWhen cooled to r.t. the mixture
  2. concentrationwas concentrated
  3. custompurified on a silica gel column
  4. washeluted with 0-50% EtOAc in heptane

Sources & evidence

ORD record
ord-ffcc6440cf50430ba030ab65c8f21c16
Source dataset
uspto-grants-2016_02
Patent number
US09248129B2

Reaction notes

Loading…