Water → 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 402299Notes

Reaction equation

HRID 402299 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].O>CN(C)C=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

5

Reactant 3

HCID 962WaterHCID 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-olateYield 64.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Raltegravir (10 gm) was dissolved in dimethylformamide (100 ml) at room temperature and cooled to 10 to 15 deg C. To the reaction mass was added slowly a mixture of potassium hydroxide (1.5 gm) and water (2 ml) at 10 to 15 deg C. and the temperature was raised to 25 to 30 deg C., filtered. The solid obtained was washed with dimethylformamide and dried at 110 to 120 deg C. for 48 hours to obtain 7 gm of raltegravir potassium crystalline form H1.

Workup

  1. temperaturecooled to 10 to 15 deg C
  2. additionTo the reaction mass was added slowly
  3. temperatureand the temperature was raised to 25 to 30 deg C
  4. filtration, filtered
  5. customThe solid obtained
  6. washwas washed with dimethylformamide
  7. customdried at 110 to 120 deg C

Sources & evidence

ORD record
ord-3b829ea35f75474ba50b59d8568d22e3
Source dataset
uspto-grants-2014_06
Patent number
US08742105B2

Reaction notes

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