Triethylamine → HCID 121386246, compound

HRID 2202891Notes

Reaction equation

HRID 2202891 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:14])=[C:9]([C:11](O)=[O:12])[N:10]=2)[CH:7]=1.C[N:16](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[NH4+].[Cl-]>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]([NH2:16])=[O:12])[N:10]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 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 121386246HCID 121386246, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-iodo-3-methylimidazo[1,2-a]pyridine-2-carboxylic acid (1.0 g) in DMF (15 ml) were added HATU (1.88 g) and triethylamine (1.38 ml) at 0° C. The mixture was allowed to warm to room temperature for 30 min, and then NH4Cl (725 mg) was added thereto. The resultant mixture was stirred at the same temperature for 18 h. The mixture was then concentrated in vacuo and diluted with DCM (100 ml). The DCM layer was successively washed with saturated aqueous NH4Cl solution, saturated aqueous NaHCO3 solution, water and brine. The DCM layer was then dried over Na2SO4 and concentrated in vacuo to give the title compound (600 mg) as a yellow solid.

Workup

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

Sources & evidence

ORD record
ord-f96aad285d154e37b150388f6cd4642e
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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