Butanethiol → HCID 67211057, compound

HRID 1727243Notes

Reaction equation

HRID 1727243 reaction equation
C(N(C(C)C)CC)(C)C.[CH2:10]([SH:14])[CH2:11][CH2:12][CH3:13].Br[C:16]1[C:17](=[O:33])[C:18]2[S:22][C:21]([CH3:23])=[N:20][C:19]=2[C:24](=[O:32])[C:25]=1[NH:26][CH2:27][CH2:28][N:29]([CH3:31])[CH3:30]>C(O)C>[CH2:10]([S:14][C:16]1[C:17](=[O:33])[C:18]2[S:22][C:21]([CH3:23])=[N:20][C:19]=2[C:24](=[O:32])[C:25]=1[NH:26][CH2:27][CH2:28][N:29]([CH3:30])[CH3:31])[CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 8012ButanethiolHCID 81531DiisopropylethylamineHCID 10215392HCID 10215392, compound

Product 1

HCID 67211057HCID 67211057, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

20 μl (0.115 mmol; 1.2 eq.) of diisopropylethylamine and 16 μl (0.154 mmol; 1.6 eq.) of butanethiol are added to 33 mg (96 μmol) of the compound of Example 35 in solution in 4 ml of anhydrous ethanol. The reaction mixture is maintained under stirring for 24 hours at 60° C., then after concentration under reduced pressure, the residue is purified by chromatography on a silica column (eluent: dichloromethane/methanol 95/5) and the expected product is obtained, after taking up in ethyl ether, in the form of a violet-coloured powder.

Workup

  1. temperatureThe reaction mixture is maintained
  2. concentrationafter concentration under reduced pressure
  3. customthe residue is purified by chromatography on a silica column (eluent: dichloromethane/methanol 95/5)

Sources & evidence

ORD record
ord-2858fa6bc35d42c7802ac1cddba65bd1
Source dataset
uspto-grants-2009_02
Patent number
US07495021B2

Reaction notes

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