Celecoxib → HCID 86605546, compound

HRID 1809978Notes

Reaction equation

HRID 1809978 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([C:13]3[CH:14]=[CH:15][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:17][CH:18]=3)[N:11]=[C:10]([C:23]([F:26])([F:25])[F:24])[CH:9]=2)=[CH:6][CH:7]=1.[CH3:27][N:28]1[CH2:32][CH2:31][CH2:30][C:29]1=[O:33]>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([C:13]3[CH:14]=[CH:15][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:17][CH:18]=3)[N:11]=[C:10]([C:23]([F:25])([F:24])[F:26])[CH:9]=2)=[CH:6][CH:7]=1.[CH3:27][N:28]1[C:29](=[O:33])[CH2:30][CH2:31][CH2:32]1

Participants

3

Reactant 2

HCID 2662CelecoxibHCID 13387N-methyl-2-pyrrolidone

Product 1

HCID 86605546HCID 86605546, compound

Conditions

Temperature
75 °C

Procedure

To solid celecoxib (127 mg; 0.333 mmol) was added N-methyl-2-pyrrolidone (0.75 mL) to give a white suspension. The mixture was heated to 75 degrees C. and held at this temperature for 3 minutes at which point the solid dissolved to give a colorless solution. The solution was cooled to room temperature and then cooled to 5 degrees C. for three days. After three days, colorless hexagonal crystals had formed. The mother liquor was decanted and the solid was suspended in pentane (2 mL) and filtered. The solid was air dried and collected. The solid was found to be a 1:1 N-Methyl-2-pyrrolidone (NMP) solvate of celecoxib.

Workup

  1. customto give a white suspension
  2. dissolutionthe solid dissolved
  3. customto give a colorless solution
  4. temperatureThe solution was cooled to room temperature
  5. temperaturecooled to 5 degrees C
  6. waitfor three days
  7. waitAfter three days
  8. customcolorless hexagonal crystals had formed
  9. customThe mother liquor was decanted
  10. filtrationfiltered
  11. customdried
  12. customcollected

Sources & evidence

ORD record
ord-adf245e43a8a4cad827432e06d97e692
Source dataset
uspto-grants-2013_01
Patent number
US08362062B2

Reaction notes

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