Trifluoroacetic acid → HCID 23155060, compound

HRID 1912872Notes

Reaction equation

HRID 1912872 reaction equation
C(O[C:6](=O)[N:7]([C:9]1[N:17]=[CH:16][N:15]=[C:14]2[C:10]=1[N:11]=[CH:12][N:13]2[C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:27][C:28]2[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[C:30]([C:38](=[O:45])[NH:39][CH:40]([CH2:43][OH:44])[CH2:41][OH:42])[CH:29]=2)=[O:26])=[CH:20][CH:19]=1)C)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+]>O>[OH:42][CH2:41][CH:40]([NH:39][C:38](=[O:45])[C:30]1[CH:31]=[C:32]([C:34]([F:35])([F:36])[F:37])[CH:33]=[C:28]([NH:27][C:25]([NH:24][C:21]2[CH:22]=[CH:23][C:18]([N:13]3[CH:12]=[N:11][C:10]4[C:14]3=[N:15][CH:16]=[N:17][C:9]=4[NH:7][CH3:6])=[CH:19][CH:20]=2)=[O:26])[CH:29]=1)[CH2:43][OH:44]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 59725991HCID 59725991, compound

Product 1

HCID 23155060HCID 23155060, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 40.8 mg (0.063 mmol) of [9-(4-{3-[3-(2-hydroxy-1-hydroxymethyl-ethyl-carbamoyl)-5-trifluoromethylphenyl]ureido}phenyl)-9H-purin-6-yl]-methyl-carbamic acid tert-butyl ester, 1 mL of trifluoroacetic acid was added and the mixture solution was stirred at room temperature for one hour. The solvent was distilled under reduced pressure from the reaction solution and the obtained residue was dissolved in methanol (1 mL) and water (60 μL), and 43.7 mg (0.315 mmol) of potassium carbonate was added thereto, and the mixture solution was stirred at room temperature for 1.5 hours. Water was added to the reaction solution and the obtained solid was collected by filtration and dried under reduced pressure to obtain 32 mg (93%) of a target product as a white solid.

Workup

  1. distillationThe solvent was distilled under reduced pressure from the reaction solution
  2. dissolutionthe obtained residue was dissolved in methanol (1 mL)
  3. stirringthe mixture solution was stirred at room temperature for 1.5 hours
  4. filtrationthe obtained solid was collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-fc3e669a40af402884bf7874d3efa131
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

Loading…