3,5-Dimethylaniline → 2-(2-tert-Butoxycarbonylaminopyridin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide

HRID 1984713

Reaction equation

HRID 1984713 reaction equation
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[C:25]([O:29][C:30]([NH:32][C:33]1[CH:38]=[C:37]([CH2:39][S:40][C:41]2[C:46]([C:47]([OH:49])=O)=[CH:45][CH:44]=[CH:43][N:42]=2)[CH:36]=[CH:35][N:34]=1)=[O:31])([CH3:28])([CH3:27])[CH3:26].[NH2:50][C:51]1[CH:56]=[C:55]([CH3:57])[CH:54]=[C:53]([CH3:58])[CH:52]=1.C(N(CC)C(C)C)(C)C>CN(C)C=O.C(OCC)(=O)C>[C:25]([O:29][C:30]([NH:32][C:33]1[CH:38]=[C:37]([CH2:39][S:40][C:41]2[C:46]([C:47]([NH:50][C:51]3[CH:56]=[C:55]([CH3:57])[CH:54]=[C:53]([CH3:58])[CH:52]=3)=[O:49])=[CH:45][CH:44]=[CH:43][N:42]=2)[CH:36]=[CH:35][N:34]=1)=[O:31])([CH3:27])([CH3:28])[CH3:26]

Participants

7

Reactant 4

HCID 79493,5-DimethylanilineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 231509762-(2-tert-Butoxycarbonylaminopyridin-4-ylmethylthio)pyridine-3-carboxylic acid

Product 1

HCID 112482792-(2-tert-Butoxycarbonylaminopyridin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (630 mg, 1.7 mmol) was added to a solution of 2-(2-tert-butoxycarbonylaminopyridin-4-ylmethylthio)pyridine-3-carboxylic acid (Reference compound No. 9-1, 500 mg, 1.4 mmol), 3,5-xylidine (180 mg, 1.5 mmol) and N,N-diisopropylethylamine (0.72 mL, 4.1 mmol) in N,N-dimethylformamide (7 mL) at room temperature, and the mixture was stirred for 12 hours. Ethyl acetate (30 mL) was added to the reaction mixture, then the whole was washed with brine (50 mL) and dried over anhydrous magnesium sulfate. The organic layer was evaporated under reduced pressure, then the resulting residue was purified by silica gel column chromatography to give 670 mg of the target compound quantitatively as a colorless solid.

Workup

  1. washthe whole was washed with brine (50 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe organic layer was evaporated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f772678dc6d54076a5ed56384050d816
Source dataset
uspto-grants-2009_06
Patent number
US07544703B2

Linked notes

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