Methanol → Methyl 2-amino-6-morpholino-3-nitroisonicotinate

HRID 1399785Notes

Reaction equation

HRID 1399785 reaction equation
[NH2:1][C:2]1[C:3]([N+:17]([O-:19])=[O:18])=[C:4]([CH:8]=[C:9]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[N:10]=1)[C:5]([OH:7])=[O:6].[CH3:20]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CO.CCN(CC)CC>C1COCC1>[NH2:1][C:2]1[C:3]([N+:17]([O-:19])=[O:18])=[C:4]([CH:8]=[C:9]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[N:10]=1)[C:5]([O:7][CH3:20])=[O:6]

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 896479892-Amino-6-morpholino-3-nitroisonicotinic acid

Product 1

HCID 89648265Methyl 2-amino-6-morpholino-3-nitroisonicotinateYield 37.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-amino-6-morpholino-3-nitroisonicotinic acid (12.3 g, 45.9 mmol), HATU (19.2 g, 50.5 mmol), MeOH (14.7 g, 459 mmol) and Et3N (13.9 g, 137.7 mmol) in THF (300 mL) was stirred at room temperature for 16 h. The solvent was removed in vacuo and the residue was diluted with EA (500 mL). It was then washed with brine (500 mL×3). The organic layer was then concentrated in vacuo. The residue was then purified by chromatography on silica gel eluted with MeOH/DCM=1/100 to afford the crude product as a yellow solid (4.8 g, 37%); LC/MS: MS (ES+) m/e 283 (MH+).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted with EA (500 mL)
  3. washIt was then washed with brine (500 mL×3)
  4. concentrationThe organic layer was then concentrated in vacuo
  5. customThe residue was then purified by chromatography on silica gel
  6. washeluted with MeOH/DCM=1/100

Sources & evidence

ORD record
ord-549ab2ed1806421dba7571cceb7d65f1
Source dataset
uspto-grants-2014_12
Patent number
US08906910B2

Reaction notes

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