Dimethylamine → HCID 54192364, compound

HRID 1480797Notes

Reaction equation

HRID 1480797 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 for 18 hours. The reaction was partitioned between EtOAc and water, the organic layers were washed with water, dried over Na2SO4 and concentrated in vacuo. The residue was purified by Biotage silica gel column chromatography eluting with DCM/EtOAc 60/40 to 40/60 followed by filtration through an SCX-2 column eluting with 2M NH3/MeOH to afford the title compound as a colourless oil (69 mg, 59%).

Workup

  1. customThe reaction was partitioned between EtOAc and water
  2. washthe organic layers were washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by Biotage silica gel column chromatography
  6. washeluting with DCM/EtOAc 60/40 to 40/60
  7. filtrationfollowed by filtration through an SCX-2 column
  8. washeluting with 2M NH3/MeOH

Sources & evidence

ORD record
ord-1949b4effd904a469e618a82708aa7e4
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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