5-Methyl-2-furanmethanethiol → HCID 9968079, compound

HRID 1789940Notes

Reaction equation

HRID 1789940 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]2[C:5]([C:6]([NH:24][C@H:25]([CH3:28])[CH2:26][OH:27])=[N:7][C:8]([S:12]([CH2:15][C:16]3C=[CH:20][CH:19]=[C:18](F)[C:17]=3F)(=O)=O)=[N:9]2)=[N:4][CH:3]=1.CC1[O:34]C(CS)=CC=1.CC(C)([O-])C.[K+]>CS(C)=O.C1COCC1>[NH2:1][C:2]1[N:11]=[C:10]2[C:5]([C:6]([NH:24][C@H:25]([CH3:28])[CH2:26][OH:27])=[N:7][C:8]([S:12][CH2:15][C:16]3[O:34][C:19]([CH3:20])=[CH:18][CH:17]=3)=[N:9]2)=[N:4][CH:3]=1

Participants

6

Reactant 3

HCID 5218735-Methyl-2-furanmethanethiolHCID 23665647Potassium tert-butoxideHCID 69463454HCID 69463454, compound

Product 1

HCID 9968079HCID 9968079, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product from example 10, step (a) (0.18 g) and 5-methyl-2-furanmethanethiol (75 mg) in anhydrous DMSO (3 ml) was treated with potassium t-butoxide solution in THF (1.0 M, 0.44 ml) and stirred at room temperature for 1 hour. The solution was purified directly by preparative reversed phase HPLC on a Waters 19×50 mm Symmetry C8 silica column eluted with 0.1% aqueous ammonium acetate:acetonitrile (70:30) to give an off-white solid that was dried under reduced pressure at 40° C. (8 mg).

Workup

  1. customThe solution was purified directly by preparative reversed phase HPLC on a Waters 19×50 mm Symmetry C8 silica column
  2. washeluted with 0.1% aqueous ammonium acetate:acetonitrile (70:30)
  3. customto give an off-white solid
  4. customthat was dried under reduced pressure at 40° C. (8 mg)

Sources & evidence

ORD record
ord-17e0d1ecf4ff4543b216d3fbe834abf2
Source dataset
uspto-grants-2006_07
Patent number
US07071193B2

Reaction notes

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