Sodium Bicarbonate → Methyl 3-({[6-amino-3,5-dicyano-4-(tetrahydro-2H-pyran-2-yl)pyridin-2-yl]thio}methyl)benzoate
Reaction equation
C(=O)(O)[O-].[Na+].[NH2:6][C:7]1[C:12]([C:13]#[N:14])=[C:11]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[C:10]([C:21]#[N:22])=[C:9]([SH:23])[N:8]=1.[CH3:24][O:25][C:26](=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33]Br)[CH:28]=1>CN(C=O)C>[NH2:6][C:7]1[N:8]=[C:9]([S:23][CH2:33][C:29]2[CH:28]=[C:27]([CH:32]=[CH:31][CH:30]=2)[C:26]([O:25][CH3:24])=[O:35])[C:10]([C:21]#[N:22])=[C:11]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[C:12]=1[C:13]#[N:14]Participants
5
Procedure
48 mg (0.58 mmol) of sodium bicarbonate are added to a solution of 50 mg (0.19 mmol) of the compound from Example 31A and 48 mg (0.21 mmol) of 3-(bromomethyl)benzoic acid methyl ester in 2 ml of dry DMF, and the mixture is stirred at RT for 20 h. The mixture is then directly purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).
Workup
- customThe mixture is then directly purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)
Sources & evidence
- ORD record
- ord-0e7a66d0d62b4f90b28cf50cdc06baa0
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08304412B2
Reaction notes
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