Sodium Bicarbonate → 2-Amino-6-({[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methyl}sulfanyl)-4-(4-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}-phenyl)pyridine-3,5-dicarbonitrile

HRID 1913493Notes

Reaction equation

HRID 1913493 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C@@H:18]3[CH2:22][O:21][C:20]([CH3:24])([CH3:23])[O:19]3)=[CH:12][CH:11]=2)[C:5]([C:25]#[N:26])=[C:4]([SH:27])[N:3]=1.Cl[CH2:29][C:30]1[N:31]=[C:32]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)[O:33][CH:34]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C@@H:18]3[CH2:22][O:21][C:20]([CH3:23])([CH3:24])[O:19]3)=[CH:12][CH:11]=2)[C:5]([C:25]#[N:26])=[C:4]([S:27][CH2:29][C:30]2[N:31]=[C:32]([C:35]3[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=3)[O:33][CH:34]=2)[N:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 71315274-(Chloromethyl)-2-(4-chlorophenyl)-1,3-oxazoleHCID 178431479HCID 178431479, compound

Product 1

HCID 666718892-Amino-6-({[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methyl}sulfanyl)-4-(4-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}-phenyl)pyridine-3,5-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

70 mg (0.18 mmol) of the compound from Example 38A and 46 mg (0.20 mmol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-oxazole together with 46 mg (0.55 mmol) of sodium bicarbonate were suspended in 1.9 ml of dry DMF. The reaction mixture was stirred at RT for 20 h. The mixture was then freed from the solvent on a rotary evaporator, and the residue was purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).

Workup

  1. customThe mixture was then freed from the solvent on a rotary evaporator
  2. customthe residue was 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-5e03c7fb92a845b59aa919ada65938b5
Source dataset
uspto-grants-2013_12
Patent number
US08609686B2

Reaction notes

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