Sodium Bicarbonate → HCID 86726460, compound

HRID 529688Notes

Reaction equation

HRID 529688 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]([OH:11])=O)[CH:6]=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].Cl.CN.C(=O)(O)[O-].[Na+].[CH3:23][N:24](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CS(C)=O>[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]([NH:24][CH3:23])=[O:11])[CH:6]=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 6364545Methylamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 225652336-Methoxy-5-nitropyridine-2-carboxylic acid

Product 1

HCID 86726460HCID 86726460, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
25 °C

Procedure

The suspension of 6-methoxy-5-nitropicolinic acid (1 equiv), methylamine hydrochloride (2 equiv), sodium bicarbonate (2 equiv), HATU (2 equiv) in DMSO (1 M) was stirred at 25° C. for 15 h. The reaction mixture was quenched with saturated aqueous sodium chloride and then washed with ethyl acetate. The organic phase was combined and washed with saturated aqueous sodium bicarbonate. The organic layer was dried (anhydrous sodium sulfate), filtered, and concentrated. The crude product was purified by silica gel column chromatography (0-90% ethyl acetate (with 1% 1N ammonia in methanol) in hexane). Concentration of the desired fractions under reduced pressure afforded the title compound (85%) as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 2.86 (d, J=4.73 Hz, 3 H) 4.17 (s, 3 H) 7.77 (dd, J=8.04, 0.79 Hz, 1 H) 8.54-8.60 (m, 1 H) 8.77 (m, J=4.10 Hz, 1 H); MS (ESI) m/z 212.2 [M+1]+.

Workup

  1. customThe reaction mixture was quenched with saturated aqueous sodium chloride
  2. washwashed with ethyl acetate
  3. washwashed with saturated aqueous sodium bicarbonate
  4. dry with materialThe organic layer was dried (anhydrous sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel column chromatography (0-90% ethyl acetate (with 1% 1N ammonia in methanol) in hexane)

Sources & evidence

ORD record
ord-cf49bf651571405c883f5e51dc6849e6
Source dataset
uspto-grants-2016_05
Patent number
US09346812B2

Reaction notes

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