Acetic Acid → HCID 58542023, compound

HRID 1966766Notes

Reaction equation

HRID 1966766 reaction equation
[C:1]([OH:4])(=O)[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[NH2:36][C:37]1[N:42]=[CH:41][C:40]([C:43]2[CH:65]=[CH:64][C:46]3[N:47]([C:60]([CH3:63])([CH3:62])[CH3:61])[C:48]([C:50]4[CH:59]=[CH:58][CH:57]=[CH:56][C:51]=4[C:52]([NH:54]O)=[NH:53])=[N:49][C:45]=3[CH:44]=2)=[CH:39][N:38]=1>CN(C=O)C>[C:60]([N:47]1[C:46]2[CH:64]=[CH:65][C:43]([C:40]3[CH:41]=[N:42][C:37]([NH2:36])=[N:38][CH:39]=3)=[CH:44][C:45]=2[N:49]=[C:48]1[C:50]1[CH:59]=[CH:58][CH:57]=[CH:56][C:51]=1[C:52]1[N:54]=[C:1]([CH3:2])[O:4][N:53]=1)([CH3:63])([CH3:61])[CH3:62]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178448433HCID 178448433, compound

Product 1

HCID 58542023HCID 58542023, compoundYield 12.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of acetic acid (30 mg, 0.5 mmol) and HATU (189 mg, 0.5 mmol) in DMF (2 mL) is added triethylamine (0.07 mL, 0.5 mmol). The reaction mixture is stirred at room temperature for 10 minutes and 2-[5-(2-amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzimidazol-2-yl]-N-hydroxy-benzamidine (200 mg, 0.5 mmol) is added. The reaction mixture is stirred at room temperature for 0.5 hours then warmed to 80° C. and stirred for 15 hours. The reaction mixture is cooled to room temperature and concentrated in vacuo. EtOAc (20 mL) is added and the organics washed with H2O (30 mL) then dried (Na2SO4), filtered and concentrated. Purification via prep HPLC (0.1% TFA/MeCN) affords the title compound (27 mg, 8%) as 2TFA salt. LCMS (ESMS): m/z 426.20 (M++1)

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 0.5 hours
  2. temperaturethen warmed to 80° C.
  3. stirringstirred for 15 hours
  4. temperatureThe reaction mixture is cooled to room temperature
  5. concentrationconcentrated in vacuo
  6. additionEtOAc (20 mL) is added
  7. washthe organics washed with H2O (30 mL)
  8. dry with materialthen dried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification via prep HPLC (0.1% TFA/MeCN)

Sources & evidence

ORD record
ord-2ba4d226df3d4ed5ad57933bb815af28
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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