Phenolate Sodium → HCID 57888981, compound

HRID 1016207Notes

Reaction equation

HRID 1016207 reaction equation
[Cl:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:32]=1)[C:7]([NH:9][C@H:10]([CH:29]([CH3:31])[CH3:30])[C:11]([N:13]1[CH2:18][CH2:17][C@@:16]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)([OH:19])[C:15]([CH3:28])([CH3:27])[CH2:14]1)=[O:12])=[O:8].[C:34]1([O-:40])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[Na+]>CN(C=O)C>[Cl:1][C:2]1[C:3]([O:40][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[N:4][CH:5]=[C:6]([CH:32]=1)[C:7]([NH:9][C@H:10]([CH:29]([CH3:30])[CH3:31])[C:11]([N:13]1[CH2:18][CH2:17][C@@:16]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)([OH:19])[C:15]([CH3:28])([CH3:27])[CH2:14]1)=[O:12])=[O:8]

Participants

4

Reactant 2

HCID 4445035Phenolate SodiumHCID 57888667HCID 57888667, compound

Product 1

HCID 57888981HCID 57888981, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5,6-Dichloro-N—((R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-yl)nicotinamide (35 mg, 0.068 mmol), 0.5 mL DMF, and sodium phenolate (9.51 mg, 0.08 mmol) was heated for 1 hr at 120° C. Example 624 was isolated as a white solid by preparative reverse phase HPLC (13.7 mg, 35.2% yield), M+H=570.07.

Workup

  1. customExample 624 was isolated as a white solid by preparative reverse phase HPLC (13.7 mg, 35.2% yield), M+H=570.07

Sources & evidence

ORD record
ord-71ba2add33ee434a9771347cc30cd180
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

Loading…