Dimethylamine → HCID 119086489, compound

HRID 2202916Notes

Reaction equation

HRID 2202916 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:14])=[C:9]([C:11]([OH:13])=O)[N:10]=2)[CH:7]=1.[CH3:15][N:16](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:17].F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.CNC>CN(C=O)C>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:14])=[C:9]([C:11]([N:16]([CH3:17])[CH3:15])=[O:13])[N:10]=2)[CH:7]=1

Participants

6

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 121386217HCID 121386217, compound

Product 1

HCID 119086489HCID 119086489, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-iodo-3-methylimidazo[1,2-a]pyridine-2-carboxylic acid (150 mg) in DMF (5 ml) were added HATU (283 mg) and N,N-diisopropylethylamine (0.17 ml) at 0° C. The mixture was allowed to warm to room temperature and stirred for 30 min. Dimethylamine (2 M in THF, 0.2 ml) was added, and the resultant mixture was stirred at the same temperature for 18 h. The mixture was then concentrated in vacuo and the residue was diluted with DCM (100 ml). The DCM layer was successively washed with saturated aqueous NH4Cl solution (40 ml), saturated aqueous NaHCO3 solution (20 ml), water (30 ml) and brine (50 ml). The DCM layer was then dried m over Na2SO4, and concentrated in vacuo to give the title compound (150 mg) as a brown oil.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. additionthe residue was diluted with DCM (100 ml)
  3. washThe DCM layer was successively washed with saturated aqueous NH4Cl solution (40 ml), saturated aqueous NaHCO3 solution (20 ml), water (30 ml) and brine (50 ml)
  4. dry with materialThe DCM layer was then dried m over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-70fbe92568c941f1b08fe40e5289bfb8
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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