Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 4-({[(3-Fluoro-4-methylphenyl)amino]carbonyl}amino)-N-[1-(6-methoxypyridin-3-yl)ethyl]-1-methyl-1H-imidazole-2-carboxamide

HRID 499914Notes

Reaction equation

HRID 499914 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.[CH3:46][O:47][C:48]1[N:53]=[CH:52][C:51]([CH:54]([NH2:56])[CH3:55])=[CH:50][CH:49]=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:56][CH:54]([C:51]3[CH:52]=[N:53][C:48]([O:47][CH3:46])=[CH:49][CH:50]=3)[CH3:55])=[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 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 586291041-(6-Methoxypyridin-3-yl)ethan-1-amineHCID 594217444-({[(4-Methyl-3-fluorophenyl)amino]carbonyl}amino)-1-methyl-1H-imidazole-2-carboxylic Acid

Product 1

HCID 113508034-({[(3-Fluoro-4-methylphenyl)amino]carbonyl}amino)-N-[1-(6-methoxypyridin-3-yl)ethyl]-1-methyl-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. 60 mg (0.39 mmol) of [1-(6-methoxypyridin-3-yl)ethyl]amine are added to this solution and the mixture is stirred overnight. The reaction mixture is purified by preparative HPLC. The correct fractions are evaporated in vacuo.

Workup

  1. stirringthe mixture is stirred overnight
  2. customThe reaction mixture is purified by preparative HPLC
  3. customThe correct fractions are evaporated in vacuo

Sources & evidence

ORD record
ord-0b32679a97ca4293a00b50f43decddc2
Source dataset
uspto-grants-2010_08
Patent number
US07767704B2

Reaction notes

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