Dimethyl Sulfide → HCID 58459336, compound

HRID 2036669Notes

Reaction equation

HRID 2036669 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:28]=[N:29][CH:30]=[CH:31][CH:32]=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]=[N:29][CH:30]=[CH:31][CH:32]=1)[CH3:13]

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 58459382HCID 58459382, compound

Product 1

HCID 58459336HCID 58459336, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The mixture of (S)-methyl 2-(1-(((benzyloxy)carbonyl)amino)ethyl)-3-(pyridin-3-yl)imidazo[1,2-a]pyridine-5-carboxylate (450 mg, 1.04 mmol) and dimethylsulfide (0.4 mL) in TFA (1.2 mL)) was stirred at rt overnight. The mixture was concentrated in vacuo. The residue was dissolved in EtOAc. The organic layer was washed with satd. sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated in vacuo to provide (S)-methyl 2-(1-aminoethyl)-3-(pyridin-3-yl)imidazo[1,2-a]pyridine-5-carboxylate: LC-MS (ESI) m/z 297.2 [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 solution, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6c45b56ebd5e4a2ea14e82275a9b8917
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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