Trimetrexate → HCID 131722762, compound

HRID 1368864Notes

Reaction equation

HRID 1368864 reaction equation
[CH3:1][C:2]1[C:7]2[C:8]([NH2:13])=[N:9][C:10]([NH2:12])=[N:11][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:14][NH:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=1.[F:28][C:29]([F:34])([F:33])[C:30]([OH:32])=[O:31]>CC(O)C.O>[CH3:1][C:2]1[C:7]2[C:8]([NH2:13])=[N:9][C:10]([NH2:12])=[N:11][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:14][NH:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=1.[F:28][C:29]([F:34])([F:33])[C:30]([O-:32])=[O:31]

Participants

5

Reactant 2

HCID 5583TrimetrexateHCID 6422Trifluoroacetic acid

Product 1

HCID 131722762HCID 131722762, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent2×

Procedure

To a suspension of 5 g of trimetrexate hydrate in 30 ml of 2-propanol and 15 ml of water was added 2.10 g of trifluoroacetic acid (approximately a 40% excess). The solid partly dissolved, but new crystals came out before it was completely gone. The mixture was heated to near reflux to give a clear dark yellow-green solution. To this was added 100 ml of 2-propanol. The product crystallized rapidly, and was collected after ice-cooling for 1 hour, washed with ice-cold 2-propanol and dried in air at 50% relative humidity to give 5.95 g of greenish-yellow crystals.

Workup

  1. dissolutionThe solid partly dissolved
  2. temperatureThe mixture was heated
  3. temperatureto near reflux
  4. customto give a clear dark yellow-green solution
  5. customThe product crystallized rapidly
  6. customwas collected after ice-
  7. temperaturecooling for 1 hour
  8. washwashed with ice-cold 2-propanol
  9. customdried in air at 50% relative humidity

Sources & evidence

ORD record
ord-18d6f636669443658976754b08772524
Source dataset
uspto-grants-2003_06
Patent number
US06576635B2

Reaction notes

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