Dimethylamine → HCID 118433819, compound

HRID 1052516Notes

Reaction equation

HRID 1052516 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=1)[C:5](O)=[O:6].[CH3:16][N:17](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:18].F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CNC>CN(C=O)C.ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=1)[C:5]([N:17]([CH3:18])[CH3:16])=[O:6]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 81562135HCID 81562135, compound

Product 1

HCID 118433819HCID 118433819, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-bromo-5-(methylsulfonamido)benzoic acid (360 mg, 1.22 mmol), HATU (490 mg, 1.29 mmol) and DIEA (260 μl, 1.49 mmol) in DMF (5 ml) was added dimethylamine (3.10 ml, 6.20 mmol, 2N in THF) and the resulting mixture was stirred at room temperature overnight. 30 ml of dichloromethane were added and washed with sodium bicarbonate 4%. The aqueous phase was further extracted with ethyl acetate. The organics were washed with water and brine, dried over magnesium sulphate and the solvent was removed to give a residue which purified by reverse phase chromatography using SP1® Purification System (C-18 silica from Waters®, water/1:1 acetonitrile-methanol as eluents [0.1% v/v formic acid buffered] 0% to 100%) to give 325 mg (83% yield) of the title compound. Purity 99%.

Workup

  1. washwashed with sodium bicarbonate 4%
  2. extractionThe aqueous phase was further extracted with ethyl acetate
  3. washThe organics were washed with water and brine
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent was removed
  6. customto give a residue which
  7. custompurified by reverse phase chromatography
  8. customSP1® Purification System (C-18 silica from Waters®, water/1:1 acetonitrile-methanol as eluents [0.1% v/v formic acid

Sources & evidence

ORD record
ord-bbba5e72982b403aa3b3612c8492a7e9
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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