3-Pyridinemethanamine → 4-({[(3-Fluoro-4-methylphenyl)amino]carbonyl}amino)-1-methyl-N-(pyridin-3-ylmethyl)-1H-imidazole-2-carboxamide

HRID 499913Notes

Reaction equation

HRID 499913 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[N:13]=[C:14]([C:18]([OH:20])=O)[N:15]([CH3:17])[CH:16]=2)=[O:10])=[CH:4][C:3]=1[F:21].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:46]1[CH:51]=[CH:50][CH:49]=[C:48]([CH2:52][NH2:53])[CH:47]=1>CN(C=O)C.CN(C1C=CN=CC=1)C>[F:21][C:3]1[CH:4]=[C:5]([NH:8][C:9]([NH:11][C:12]2[N:13]=[C:14]([C:18]([NH:53][CH2:52][C:48]3[CH:47]=[N:46][CH:51]=[CH:50][CH:49]=3)=[O:20])[N:15]([CH3:17])[CH:16]=2)=[O:10])[CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

6

Reactant 3

HCID 310183-PyridinemethanamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 594217444-({[(4-Methyl-3-fluorophenyl)amino]carbonyl}amino)-1-methyl-1H-imidazole-2-carboxylic Acid

Product 1

HCID 594217604-({[(3-Fluoro-4-methylphenyl)amino]carbonyl}amino)-1-methyl-N-(pyridin-3-ylmethyl)-1H-imidazole-2-carboxamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

60 mg (0.2 mmol) of 4-({[(4-methyl-3-fluorophenyl)amino]carbonyl}amino)-1-methyl-1H-imidazole-2-carboxylic acid (Example 18A) are dissolved in 4 ml of DMF and, after addition of 150 mg (0.39 mmol) of HATU and 36 mg (0.3 mmol) of DMAP, stirred at room temperature for 15 minutes. 43 mg (0.39 mmol) of (pyridin-3-ylmethyl)amine are added dropwise to this solution, and the mixture is stirred overnight. The reaction mixture is purified by preparative HPLC.

Workup

  1. stirringthe mixture is stirred overnight
  2. customThe reaction mixture is purified by preparative HPLC

Sources & evidence

ORD record
ord-167056d0b9824a29abac8af320355eae
Source dataset
uspto-grants-2010_08
Patent number
US07767704B2

Reaction notes

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