Acetic Acid → HCID 68522763, compound

HRID 1863964Notes

Reaction equation

HRID 1863964 reaction equation
C([O:5][C:6](=O)[NH:7][C@H:8]([CH2:23][C:24]1[CH:29]=[C:28]([F:30])[C:27]([F:31])=[CH:26][C:25]=1[F:32])[CH2:9][C:10](=O)[NH:11][NH:12][C:13]1[N:18]2[N:19]=[CH:20][N:21]=[C:17]2[CH:16]=[CH:15][N:14]=1)(C)(C)C.[C:34](O)(=O)C>>[N:12]1[N:11]=[C:10]([CH2:9][C@H:8]([NH:7][C:6](=[O:5])[CH3:34])[CH2:23][C:24]2[CH:29]=[C:28]([F:30])[C:27]([F:31])=[CH:26][C:25]=2[F:32])[N:14]2[CH:15]=[CH:16][C:17]3=[N:21][CH:20]=[N:19][N:18]3[C:13]=12

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 91551434HCID 91551434, compound

Product 1

HCID 68522763HCID 68522763, compound

Procedure

A solution of 93.1 mg (0.2 mmol) of tert-butyl[(1R)-3-oxo-3-(2-[1,2,4]triazolo[1,5-c]pyrimidin-5-ylhydrazino)-1-(2,4,5-trifluorobenzyl)propyl]carbamate in 10 mL of glacial acetic acid was stirred at reflux under nitrogen for 40 h. The cooled solution was concentrated, and the residue was partitioned between 5 mL of ethyl acetate and 3 mL of saturated sodium carbonate aqueous solution. The organic phase was dried over magnesium sulfate, filtered, and concentrated to dryness. The residue was purified by preparative thin-layer chromatography on silica gel (92.5:7.5 dichloromethane:methanol), giving the title compound as a white solid, mp 233-235° C. LC-MS 390 (M+1).

Workup

  1. temperatureat reflux under nitrogen for 40 h
  2. concentrationThe cooled solution was concentrated
  3. customthe residue was partitioned between 5 mL of ethyl acetate and 3 mL of saturated sodium carbonate aqueous solution
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by preparative thin-layer chromatography on silica gel (92.5:7.5 dichloromethane:methanol)

Sources & evidence

ORD record
ord-1a5af77e1d0f4e0892091b411822a056
Source dataset
uspto-grants-2009_12
Patent number
US07625888B2

Reaction notes

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