Acetic Acid → methyl 2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate

HRID 1399787Notes

Reaction equation

HRID 1399787 reaction equation
[NH2:1][C:2]1[C:3]([NH2:18])=[C:4]([CH:9]=[C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:19][C:20](O)=O>>[CH3:19][C:20]1[NH:1][C:2]2=[N:11][C:10]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]2[N:18]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 89647670Methyl 2,3-diamino-6-morpholinoisonicotinate2×

Product 1

HCID 178498376methyl 2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate

Procedure

A solution of methyl 2,3-diamino-6-morpholinoisonicotinate (4.3 g, 17 mmol) in CH3COOH (100 mL) was refluxed for 16 h. LCMS showed no methyl 2,3-diamino-6-morpholinoisonicotinate left and the desired product formed. It was cooled to room temperature and the solvent was removed in vacuo. The residue was then purified by chromatography on silica gel eluted with MeOH/DCM=1/50 to afford the desired product as a black solid (1.07 g, 23%); LC/MS: MS (ES+) m/e 277 (MH+); 1H NMR (300 MHz, CDCl3) δ ppm 2.69 (s, 3H), 3.58 (t, J=4.8 Hz, 4H), 3.86 (t, J=4.8 Hz, 4H), 4.02 (s, 3H), 7.12 (s, 1H).

Workup

  1. waitleft

Sources & evidence

ORD record
ord-f461234f0c7049f1ab344eeb3c60664c
Source dataset
uspto-grants-2014_12
Patent number
US08906910B2

Reaction notes

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