Methyl Glycolate → HCID 178510526, compound

HRID 2369210Notes

Reaction equation

HRID 2369210 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:5]([C:16]#[N:17])=[C:4]([S:18][CH2:19][C:20]2[N:21]=[C:22]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[S:23][CH:24]=2)[N:3]=1.CC(C)([O-:35])C.[K+].C(OC)(=O)CO>CN(C=O)C>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([C:22]2[S:23][CH:24]=[C:20]([CH2:19][S:18][C:4]3[C:5]([C:16]#[N:17])=[C:6]([N:10]4[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]4)[C:7]([C:8]#[N:9])=[C:2]([OH:35])[N:3]=3)[N:21]=2)=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 66774Methyl GlycolateHCID 23665647Potassium tert-butoxideHCID 866400092-Chloro-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulfanyl)-4-piperidin-1-ylpyridine-3,5-dicarbonitrile

Product 1

HCID 178510526HCID 178510526, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

400 mg (0.82 mmol) of the compound from Example 4A are initially charged in 8 ml of dry DMF. After addition of 110 mg (0.99 mmol) of potassium tert-butoxide, the mixture is stirred at RT for RT. A solution of 74 mg (0.82 mmol) of methyl glycolate in 1 ml of dry DMF is then added dropwise, and the reaction mixture is stirred at RT for 20 h. The solvent is then removed on a rotary evaporator and the residue is 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. stirringthe reaction mixture is stirred at RT for 20 h
  2. customThe solvent is then removed on a rotary evaporator
  3. customthe residue is 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-5c3da02de5934ec090b4ed228a7b345a
Source dataset
uspto-grants-2014_04
Patent number
US08703934B2

Reaction notes

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