5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]thio]-1H-imidazo[4,5b]pyridine → (S)-Tenatoprazole

HRID 490960Notes

Reaction equation

HRID 490960 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[N:9]=[C:10]([S:12][CH2:13][C:14]3[C:19]([CH3:20])=[C:18]([O:21][CH3:22])[C:17]([CH3:23])=[CH:16][N:15]=3)[NH:11][C:6]2=[CH:5][CH:4]=1.[O-:24]O.C1(C(C)C)C=CC=CC=1>CN(C=O)C>[CH3:23][C:17]1[C:18]([O:21][CH3:22])=[C:19]([CH3:20])[C:14]([CH2:13][S@@:12]([C:10]2[NH:11][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[N:8][C:7]=3[N:9]=2)=[O:24])=[N:15][CH:16]=1

Participants

4

Reactant 2

HCID 98404895-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]thio]-1H-imidazo[4,5b]pyridineHCID 53627471Cumen hydroperoxide

Product 1

HCID 11552393(S)-Tenatoprazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

A solution in DMF (6 volumes) of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]thio]imidazo[4,5-b]pyridine (100 mg, 0.303 mmol) is added under stirring at 20° C., immediately followed by cumene hydroperoxide (80%, 65 μL, 0.352 mmol)

Sources & evidence

ORD record
ord-c2c6404b4ca44b76ba0e84335ada5efa
Source dataset
uspto-grants-2009_05
Patent number
US07528251B2

Reaction notes

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