Sodium Bicarbonate → 2-Amino-4-(4-{[(2S)-2-{[tert-butyl(dimethyl)silyl]oxy}propyl]oxy}phenyl)-6-({[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]methyl}thio)pyridine-3,5-dicarbonitrile

HRID 508172Notes

Reaction equation

HRID 508172 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]([O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH3:19])=[CH:12][CH:11]=2)[C:5]([C:28]#[N:29])=[C:4]([SH:30])[N:3]=1.Cl[CH2:32][C:33]1[N:34]=[C:35]([C:39]2[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=2)[O:36][C:37]=1[CH3:38].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:11]=[CH:12][C:13]([O:16][CH2:17][C@@H:18]([O:20][Si:21]([C:24]([CH3:25])([CH3:26])[CH3:27])([CH3:22])[CH3:23])[CH3:19])=[CH:14][CH:15]=2)[C:5]([C:28]#[N:29])=[C:4]([S:30][CH2:32][C:33]2[N:34]=[C:35]([C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)[O:36][C:37]=2[CH3:38])[N:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 106092554-(Chloromethyl)-2-(4-fluorophenyl)-5-methyl-1,3-oxazoleHCID 178461775HCID 178461775, compound

Product 1

HCID 672153962-Amino-4-(4-{[(2S)-2-{[tert-butyl(dimethyl)silyl]oxy}propyl]oxy}phenyl)-6-({[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]methyl}thio)pyridine-3,5-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg (0.18 mmol) of the compound from Example 7A, 45 mg (0.20 mmol) of 4-(chloromethyl)-2-(4-fluorophenyl)-5-methyl-1,3-oxazole and 46 mg (0.55 mmol) of sodium bicarbonate in 2 ml of dry DMF are stirred at RT for 20 h. The mixture is purified directly by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5). Removal of the solvent on a rotary evaporator gives the product as a white solid.

Workup

  1. customThe mixture is purified directly by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)
  2. customRemoval of the solvent
  3. customon a rotary evaporator

Sources & evidence

ORD record
ord-d42f07e795de498085f626ce02079b8a
Source dataset
uspto-grants-2015_08
Patent number
US09095582B2

Reaction notes

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