Methanamine, N-methoxy-, hydrochloride (1:1) → 2-Amino-3-phenyl-6-(N-methyl-N-methoxycarbamoyl)imidazo[1,2-a]pyridine

HRID 277929Notes

Reaction equation

HRID 277929 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([C:10]([OH:12])=O)=[CH:6][N:5]2[C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl.[CH3:21][NH:22][O:23][CH3:24].C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[NH2:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([C:10](=[O:12])[N:22]([CH3:21])[O:23][CH3:24])=[CH:6][N:5]2[C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 226267402-Amino-3-phenyl-6-(carboxy)imidazo[1,2-a]pyridine

Product 1

HCID 226266852-Amino-3-phenyl-6-(N-methyl-N-methoxycarbamoyl)imidazo[1,2-a]pyridineYield 59.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The 2-amino-3-phenyl-6-(carboxy)imidazo-[1,2-a]-pyridine (80.4 g, 0.317 mol) and N,O-dimethylhydroxylamine hydrochloride (92.8 g, 0.951 mol) were dissolved in 500 ml DMF under N2. The diisopropylethylamine (123 g, 0.951 mol) was added and the mixture stirred for 30 minutes at RT. The 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (122 g, 0.634 mol) was added and allowed to stir for 19 hours at RT. The DMF was removed in vacuo and the residue was poured onto 4 L of H2O. The aqueous layer was extracted with CH2Cl2 (3×500 ml) and the organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was taken up in 400 ml of EtOAc and stirred for 1 hour at RT to form the precipitate. The precipitate was filtered and washed with cold EtOAc. The filter cake was dried in vacuo at 40° C. to yield 55.5 g of product. (59.2%). MS(FD), NMR.

Workup

  1. stirringto stir for 19 hours at RT
  2. customThe DMF was removed in vacuo
  3. additionthe residue was poured onto 4 L of H2O
  4. extractionThe aqueous layer was extracted with CH2Cl2 (3×500 ml)
  5. washthe organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. stirringstirred for 1 hour at RT
  10. customto form the precipitate
  11. filtrationThe precipitate was filtered
  12. washwashed with cold EtOAc
  13. customThe filter cake was dried in vacuo at 40° C.

Sources & evidence

ORD record
ord-98c458e40b9d403f945b9e83284834df
Source dataset
uspto-grants-2002_03
Patent number
US06358971B1

Reaction notes

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