Sodium Bicarbonate → HCID 178455313, compound

HRID 1873565Notes

Reaction equation

HRID 1873565 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH:10]2[CH2:15][CH2:14][CH:13]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:12][CH2:11]2)[C:5]([C:24]#[N:25])=[C:4]([SH:26])[N:3]=1.Cl[CH2:28][C:29]1[N:30]=[C:31]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=2)[S:32][CH:33]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C@H:10]2[CH2:11][CH2:12][C@H:13]([O:16][Si:17]([C:20]([CH3:22])([CH3:23])[CH3:21])([CH3:18])[CH3:19])[CH2:14][CH2:15]2)[C:5]([C:24]#[N:25])=[C:4]([S:26][CH2:28][C:29]2[N:30]=[C:31]([C:34]3[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=3)[S:32][CH:33]=2)[N:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 6102974-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazoleHCID 1784550312-Amino-4-(4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-6-mercaptopyridine-3,5-dicarbonitrile

Product 1

HCID 178455313HCID 178455313, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

23 mg (0.06 mmol) of the compound from Example 12A (trans isomer), 17 mg (0.07 mmol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole and 20 mg (0.24 mmol) of sodium bicarbonate are initially charged in 2 ml of dry DMF and 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

  1. 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-f5a0983d625547e292cff709268d956b
Source dataset
uspto-grants-2012_11
Patent number
US08304412B2

Reaction notes

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