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 1023665Notes

Reaction equation

HRID 1023665 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]>CN1CCCC1=O>[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 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

A vial (20 ml) was charged with Raltegravir free hydroxy (500 mg) completely dissolved in N-methyl-pyrrolidone (NMP) (1.5 ml) at room temperature. A solution of 30% aqueous KOH (0.162 ml) was added. The mixture was stirred for 21 h at room temperature. Additional NMP (7.5 ml) was added and the mixture was stirred for an additional 6.5 h at room temperature. A solid precipitated and was filtered under reduced pressure to provide wet Raltegravir potassium crystalline Form IV. The wet product was dried overnight in a vacuum oven at 40° C. to provide Raltegravir potassium crystalline Form IV.

Workup

  1. stirringthe mixture was stirred for an additional 6.5 h at room temperature
  2. customA solid precipitated
  3. filtrationwas filtered under reduced pressure

Sources & evidence

ORD record
ord-910def8e009a426b9c3bf43c76b198fa
Source dataset
uspto-grants-2014_05
Patent number
US08722722B2

Reaction notes

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