Triethylamine → N-Methoxy-N-methylthieno[3,2-c]pyridine-2-carboxamide

HRID 1890517Notes

Reaction equation

HRID 1890517 reaction equation
[S:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH:3]=[C:2]1[C:10]([OH:12])=O.CCN(CC)CC.CN([C:23]([O:27][N:28]1N=NC2C=CC=N[C:29]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.CNOC>C(Cl)Cl.CN(C=O)C>[CH3:23][O:27][N:28]([CH3:29])[C:10]([C:2]1[S:1][C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH:3]=1)=[O:12]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 13580293Thieno[3,2-c]pyridine-2-carboxylic acid

Product 1

HCID 86671431N-Methoxy-N-methylthieno[3,2-c]pyridine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of thieno[3,2-c]pyridine-2-carboxylic acid (D′-1) (11.5 g, 64.2 mmol) in DCM (200 mL) and DMF (50 mL) was added Et3N (19.5 g, 26.6 mL, 192.6 mmol) followed by HATU (36.6 g, 96.3 mmol). The reaction solution was stirred at room temperature for 20 mins, and then treated with N,O-dimethylhydroxylamine hydrochloride (6.9 g, 70.6 mmol). Stirring continued overnight at room temperature. The solvent was removed. The residue was dissolved in EtOAc and washed with water and brine. The organic layer was dried and concentrated. The residue was purified by chromatography on silica gel to give the title compound. MS (m/z): 223 (M+1)+.

Workup

  1. stirringStirring
  2. waitcontinued overnight at room temperature
  3. customThe solvent was removed
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with water and brine
  6. customThe organic layer was dried
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e6c45ab05544423b939eb2dd8c7d8675
Source dataset
uspto-grants-2013_08
Patent number
US08507487B2

Reaction notes

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