Potassium Hydroxide → Potassium 4-[{[(4-fluorophenyl)methyl]imino}(hydroxy)methyl]-1-methyl-2-{2-[(5-methyl-1,3,4-oxadiazole-2-carbonyl)amino]propan-2-yl}-6-oxo-1,6-dihydropyrimidin-5-olate

HRID 1023671Notes

Reaction equation

HRID 1023671 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]([NH:9][C:10]([C:13]2[N:19]([CH3:20])[C:17](=[O:18])[C:16]([OH:21])=[C:15]([C:22]([NH:24][CH2:25][C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=3)=[O:23])[N:14]=2)([CH3:12])[CH3:11])=[O:8])=[N:4][N:3]=1.[OH-].[K+:34]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[O:6][C:5]([C:7]([NH:9][C:10]([C:13]2[N:19]([CH3:20])[C:17](=[O:18])[C:16]([O-:21])=[C:15]([C:22]([NH:24][CH2:25][C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=3)=[O:23])[N:14]=2)([CH3:12])[CH3:11])=[O:8])=[N:4][N:3]=1.[K+:34]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 54671008Raltegravir

Product 1

HCID 23668479Potassium 4-[{[(4-fluorophenyl)methyl]imino}(hydroxy)methyl]-1-methyl-2-{2-[(5-methyl-1,3,4-oxadiazole-2-carbonyl)amino]propan-2-yl}-6-oxo-1,6-dihydropyrimidin-5-olate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A vial (20 ml) equipped with a magnetic stirrer was charged with Raltegravir free (250 mg) and toluene (2.5 mL). A clear solution was obtained. KOH 30% (80 μL) was added at room temperature and the reaction was stirred for five hours. A solid precipitate formed and was separated by filtration. The product was dried in a vacuum oven at 45° C. for overnight to obtain Raltegravir potassium Form XIV.

Workup

  1. customA vial (20 ml) equipped with a magnetic stirrer
  2. customA clear solution was obtained
  3. customA solid precipitate formed
  4. customwas separated by filtration
  5. customThe product was dried in a vacuum oven at 45° C. for overnight

Sources & evidence

ORD record
ord-5c09e58594c64441becde7084de4de68
Source dataset
uspto-grants-2014_05
Patent number
US08722722B2

Reaction notes

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