Dimethylamine → HCID 54192364, compound

HRID 2205868Notes

Reaction equation

HRID 2205868 reaction equation
[CH3:1][N:2](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:3].F[P-](F)(F)(F)(F)F.[NH2:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][C:27]=1[O:35][CH3:36].CCN(C(C)C)C(C)C.CNC>C1COCC1>[NH2:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([N:2]([CH3:3])[CH3:1])=[O:31])=[CH:28][C:27]=1[O:35][CH3:36]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 2880572486-69-3HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 54192364HCID 54192364, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

HATU (0.296 g, 0.778 mmol) was added to a solution of 4-amino-3-methoxybenzoic acid (0.1 g, 0.598 mmol), DIPEA (0.156 mL, 0.897 mmol) and dimethylamine (2M in THF, 0.598 mL, 1.196 mmol) in THF (1.617 ml). The reaction mixture was stirred overnight. It was then partitioned between EtOAc and water. The separated organic phase was washed with water, dried over Na2SO4 and evaporated in vacuum. The crude was purified via Biotage (DCM/EtOAc 60/40 to 40/60; 25 g column) and was then filtered on SCX-2 column to afford the title compound as a colourless oil (69 mg, 59%). 1H NMR (500 MHz, CDCl3) 3.06 (s, 6H), 3.87 (s, 1H), 3.99 (br s, 2H), 6.65 (d, J=7.9 Hz, 1H), 6.89 (dd, J=7.9, 1.7 Hz, 1H), 6.96 (d, J=1.7 Hz).

Workup

  1. customIt was then partitioned between EtOAc and water
  2. washThe separated organic phase was washed with water
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuum
  5. customThe crude was purified via Biotage (DCM/EtOAc 60/40 to 40/60; 25 g column)
  6. filtrationwas then filtered on SCX-2 column

Sources & evidence

ORD record
ord-ef28cdcafe0e4327a3b029d7e523f235
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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