1H-1,2,4-Triazole → HCID 86705230, compound

HRID 879184Notes

Reaction equation

HRID 879184 reaction equation
CS(O[C@@H:6]1[C@@H:11]([CH3:12])[CH2:10][N:9]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[NH:19]C(OC(C)(C)C)=O)[CH2:8][C@H:7]1[NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])(=O)=O.[NH:35]1[CH:39]=[N:38][CH:37]=[N:36]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[NH2:19][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:13]=1[N:9]1[CH2:10][C@H:11]([CH3:12])[C@H:6]([N:35]2[CH:39]=[N:38][CH:37]=[N:36]2)[C@H:7]([NH:27][C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34])[CH2:8]1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 10796Cesium carbonateHCID 86705231HCID 86705231, compound

Product 1

HCID 86705230HCID 86705230, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of (3R,4R,5S)-3-(tert-butoxycarbonylamino)-1-(3-(tert-butoxycarbonylamino)pyridin-4-yl)-5-methylpiperidin-4-yl methanesulfonate (1.0 equiv.), 1H-1,2,4-triazole (3.0 equiv.) and Cs2CO3 (3.0 equiv.) in DMF (0.17 M) was stirred at 90° C. for 3 hrs. The mixture was diluted with DMF, filtered and purified by RP HPLC, followed by free basing by partitioning between an equal volume of EtOAc and Na2CO3, separating, washing with NaCl(sat.), drying over MgSO4, filtering, concentrating to yield tert-butyl (3R,4S,5S)-1-(3-aminopyridin-4-yl)-5-methyl-4-(1H-1,2,4-triazol-1-yl)piperidin-3-ylcarbamate in 8% yield. LC/MS (m/z)=374.3 (MH+), Rt=0.53 min.

Workup

  1. filtrationfiltered
  2. custompurified by RP HPLC
  3. customby partitioning between an equal volume of EtOAc and Na2CO3
  4. customseparating
  5. washwashing with NaCl(sat.)
  6. dry with materialdrying over MgSO4
  7. filtrationfiltering
  8. concentrationconcentrating

Sources & evidence

ORD record
ord-6daec4a56d634f34aeeb15ef308cd563
Source dataset
uspto-grants-2015_03
Patent number
US08987457B2

Reaction notes

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