Potassium Carbonate → 6,7-Dimethyl-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalene

HRID 30259Notes

Reaction equation

C([N:8]1[CH2:15][CH:14]2[CH:10]([CH:11]([CH3:20])[C:12]3[C:18]([CH3:19])=[CH:17][S:16][C:13]=32)[CH2:9]1)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].CC(Cl)OC(Cl)=O>ClC(Cl)C>[CH3:19][C:18]1[C:12]2[CH:11]([CH3:20])[CH:10]3[CH:14]([C:13]=2[S:16][CH:17]=1)[CH2:15][NH:8][CH2:9]3

Participants

Conditions

Temperature: 22 °C

Procedure

The product of step h) (948 mg, 3.35 mmol) in dichloroethane (17 ml) was treated with K2CO3 (1.85 g, 13.4 mmol) and Ace-Cl (1.45 ml, 13.4 mmol) at 80° C. for 16 hours. Next, the reaction mixture was filtered, concentrated and the residue was dissolved in anhydrous MeOH (25 ml) and stirred for 1 hour at 22° C. The MeOH was concentrated and triturated with ether producing 733 mg (95%) of the subtitle compound. 1H NMR (300 MHz, d6-DMSO, ppm) 1.27 (d, J=7 Hz, 3H); 2.97-3.10 (m, 1H); 3.19-3.38 (m, 2H); 3.42-3.62 (m, 3H); 3.78-3.88 (m, 1H); 6.92 (d, J=5 Hz, 1H); 7.47 (d, J=5 Hz, 1H); 9.05 (br s, 1H); 9.38 (br s, 1H); MS calculated for C11H15NS+H 194, observed 194.

Workup

filtrationNext, the reaction mixture was filtered
concentrationconcentrated
dissolutionthe residue was dissolved in anhydrous MeOH (25 ml)
concentrationThe MeOH was concentrated
customtriturated with ether producing 733 mg (95%) of the subtitle compound

Sources & evidence

ORD record: ord-6112234434874700983433f37829ac59
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423056B2

Reaction notes

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