Dimethyl Disulfide → HCID 58456641, compound

HRID 41871Notes

Reaction equation

HRID 41871 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[CH:9][N:10]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[N:20]=4)=[CH:15][CH:14]=3)[N:11]=[C:5]2[N:4]2[C@H:26]3[CH2:31][CH2:30][CH2:29][C@H:27]3[N:28]=[C:3]12.[CH3:32][S:33]SC.[Li+].CC([N-]C(C)C)C>C1COCC1>[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[C:9]([S:33][CH3:32])[N:10]([CH2:12][C:13]3[CH:14]=[CH:15][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[N:20]=4)=[CH:17][CH:18]=3)[N:11]=[C:5]2[N:4]2[C@H:26]3[CH2:31][CH2:30][CH2:29][C@H:27]3[N:28]=[C:3]12

Participants

5

Reactant 3

HCID 12232Dimethyl DisulfideHCID 2724682Lithium diisopropylamideHCID 67434972HCID 67434972, compound

Product 1

HCID 58456641HCID 58456641, compoundYield 12.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-2-(4-(6-fluoropyridin-2-yl)benzyl)-cyclopent[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(2H)-one (50 mg, 0.12 mmol) and methyl disulfide (21.3 μL, 0.24 mmol) are dissolved in 1 mL of anhydrous THF, and then 360 uL of 1.0 M LDA in THF is added dropwise. The reaction mixture is stirred at room temperature for an hour, and then quenched with saline. The mixture is separated with a semi-preparative HPLC to give 6.8 mg of pure product as pale yellow solids. MS (ESI) m/z 463.2 [M+H]+.

Workup

  1. customquenched with saline
  2. customThe mixture is separated with a semi-preparative HPLC

Sources & evidence

ORD record
ord-147016fcb4b449cda8060539ed7edc36
Source dataset
uspto-grants-2013_09
Patent number
US08536159B2

Reaction notes

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