Aniline → Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

HRID 930491Notes

Reaction equation

HRID 930491 reaction equation
[NH2:1][C:2]1C=CC=CC=1.[CH2:8]([N:10]([CH2:13]C)[CH2:11]C)C.[F:15][P-:16]([F:21])([F:20])([F:19])([F:18])[F:17].CN(C(N(C)C)=[N+:26]1[C:34]2[C:29](=[N:30][CH:31]=[CH:32][CH:33]=2)[N+:28]([O-:35])=[N:27]1)C.[CH2:39](Cl)Cl>>[CH3:8][N:10]([C:13]([O:35][N:28]1[N:27]=[N:26][C:34]2[CH:33]=[CH:32][CH:31]=[N:30][C:29]1=2)=[N+:1]([CH3:2])[CH3:39])[CH3:11].[F:15][P-:16]([F:21])([F:20])([F:19])([F:18])[F:17]

Participants

5

Reactant 4

HCID 6115AnilineHCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 178484293HCID 178484293, compound

Product 1

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Procedure

To a solution of the aniline (1 equivalent) and the carboxylic acid (1.1 equivalent) in DCM is added triethylamine (1.5 eq) and 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU, 1.1 equivalent). The reaction mixture is stirred at RT for 3 hours, diluted with DCM, and washed with water and brine. The organic layer is concentrated.

Workup

  1. washwashed with water and brine
  2. concentrationThe organic layer is concentrated

Sources & evidence

ORD record
ord-a0cc962bc1054c588357857c25b55cd5
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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