Methylamine → 6'-{[(ethylamino)carbonyl]amino}-N-methyl-4'-(4-phenyl-1,3-thiazol-2-yl)-3,3'-bipyridine-5-carboxamide

HRID 2243038Notes

Reaction equation

HRID 2243038 reaction equation
[CH3:1][N:2](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CN.[CH2:36]([NH:38][C:39]([NH:41][C:42]1[N:47]=[CH:46][C:45]([C:48]2[CH:49]=[N:50][CH:51]=[C:52]([C:54]([OH:56])=O)[CH:53]=2)=[C:44]([C:57]2[S:58][CH:59]=[C:60]([C:62]3[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=3)[N:61]=2)[CH:43]=1)=[O:40])[CH3:37]>CN(C=O)C>[CH2:36]([NH:38][C:39]([NH:41][C:42]1[N:47]=[CH:46][C:45]([C:48]2[CH:49]=[N:50][CH:51]=[C:52]([C:54]([NH:2][CH3:1])=[O:56])[CH:53]=2)=[C:44]([C:57]2[S:58][CH:59]=[C:60]([C:62]3[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=3)[N:61]=2)[CH:43]=1)=[O:40])[CH3:37]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 592083416'-{[(Ethylamino)carbonyl]amino}-4'-(4-phenyl-1,3-thiazol-2-yl)-3,3'-bipyridine-5-carboxylic acid

Product 1

HCID 592084636'-{[(ethylamino)carbonyl]amino}-N-methyl-4'-(4-phenyl-1,3-thiazol-2-yl)-3,3'-bipyridine-5-carboxamideYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (73.7 mg, 0.19 mmol), DIEA (78.6 mg, 0.45 mmol) and methylamine (2M soln in THF, 0.15 mL, 0.30 mmol) were added to a solution of 6′-{[(ethylamino)carbonyl]amino}-4′-(4-phenyl-1,3-thiazol-2-yl)-3,3′-bipyridine-5-carboxylic acid (Example 132, 66.4 mg, 0.15 mmol) in DMF (1.5 mL). The resulting light yellow solution was stirred at room temperature for three hours. The reaction mixture was partitioned between water and ethyl acetate and layers separated. The organic layer was washed with saturated NaHCO3, water, brine, then dried over magnesium sulfate. The solvent was removed and the resulting residue was washed with acetonitrile and filtered to yield 33 mg of the title compound.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate and layers
  2. customseparated
  3. washThe organic layer was washed with saturated NaHCO3, water, brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed
  6. washthe resulting residue was washed with acetonitrile
  7. filtrationfiltered

Sources & evidence

ORD record
ord-4362ef5210c24d3b85c0d51b94ca5be1
Source dataset
uspto-grants-2010_03
Patent number
US07674801B2

Reaction notes

Loading…