Dimethyl Sulfide → HCID 58459106, compound

HRID 2036653Notes

Reaction equation

HRID 2036653 reaction equation
C(OC([NH:11][C@H:12]([C:14]1[N:15]=[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([O:24][CH3:25])=[O:23])[N:17]2[C:26]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH3:13])=O)C1C=CC=CC=1.CSC>C(O)(C(F)(F)F)=O>[NH2:11][C@H:12]([C:14]1[N:15]=[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([O:24][CH3:25])=[O:23])[N:17]2[C:26]=1[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH3:13]

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 58459381HCID 58459381, compound

Product 1

HCID 58459106HCID 58459106, compoundYield 104.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
25 °C

Procedure

The mixture of (S)-methyl 2-(1-(((benzyloxy)carbonyl)amino)ethyl)-3-phenylimidazo[1,2-a]pyridine-5-carboxylate (600 mg, 1.3 mmol) and dimethylsulfide (0.4 mL) in TFA (1.2 mL) was stirred at 25° C. overnight. The mixture was concentrated in vacuo and the residue was dissolved in EtOAc. The organic layer was washed with satd. sodium bicarbonate, dried over sodium sulfate, filtered and concentrated in vacuo to provide (S)-methyl 2-(1-aminoethyl)-3-phenylimidazo-[1,2-a]pyridine-5-carboxylate (400 mg): LC-MS (ESI) m/z 296.2 [M+H]+. The crude product was used without further purification.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in EtOAc
  3. washThe organic layer was washed with satd
  4. dry with materialsodium bicarbonate, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a1b42702a7b545a88c95125f3cdaed39
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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