[2-Amino-6-(4-ethyl-oxazol-2-yl)-3-nitro-pyridin-4-yl]-(6-methyl-pyridin-3-ylmethyl)-carbamic acid ethyl ester → 4-amino-6-(4-ethyloxazol-2-yl)-1-[(6-methyl-3-pyridyl)methyl]-3H-imidazo[4,5-c]pyridin-2-one

HRID 639608Notes

Reaction equation

HRID 639608 reaction equation
C([O:3][C:4](=O)[N:5]([C:14]1[CH:19]=[C:18]([C:20]2[O:21][CH:22]=[C:23]([CH2:25][CH3:26])[N:24]=2)[N:17]=[C:16]([NH2:27])[C:15]=1[N+:28]([O-])=O)[CH2:6][C:7]1[CH:8]=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=1)C>C(O)(=O)C.[Zn]>[NH2:27][C:16]1[C:15]2[NH:28][C:4](=[O:3])[N:5]([CH2:6][C:7]3[CH:8]=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=3)[C:14]=2[CH:19]=[C:18]([C:20]2[O:21][CH:22]=[C:23]([CH2:25][CH3:26])[N:24]=2)[N:17]=1

Participants

4

Reactant 1

HCID 67457813[2-Amino-6-(4-ethyl-oxazol-2-yl)-3-nitro-pyridin-4-yl]-(6-methyl-pyridin-3-ylmethyl)-carbamic acid ethyl ester

Product 1

HCID 497716524-amino-6-(4-ethyloxazol-2-yl)-1-[(6-methyl-3-pyridyl)methyl]-3H-imidazo[4,5-c]pyridin-2-oneYield 52.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

[2-amino-6-(4-ethyl-oxazol-2-yl)-3-nitro-pyridin-4-yl]-(6-methyl-pyridin-3-ylmethyl)-carbamic acid ethyl ester (74 mg) was dissolved in acetic acid (2 ml) and zinc powder (113 mg, Aldrich, 99%) was added to the reaction. The mixture was left to stir at room temperature under nitrogen for 16 hours. The reaction mixture was filtered directly onto a cation exchange cartridge (Bakerbond SCX, sulphonic acid bonded-phase, 1 g). The SCX cartridge was washed with methanol (2×4 ml) to remove impurities, then the product released with ammonia in methanol (2 M, 4 ml). The desired fractions were combined and evaporated to an off-white solid that was triturated with isopropanol, filtered, and then washed with isopropanol, providing the title compound (32 mg) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.16 (t, J=7.42 Hz, 3 H) 2.40 (s, 3 H) 2.44-2.56 (m, 2 H) 5.04 (s, 2 H) 5.98 (s, 2 H) 7.19 (d, J=8.02 Hz, 1 H) 7.23 (s, 1 H) 7.54 (dd, J=8.02, 2.34 Hz, 1 H) 7.79 (s, 1 H) 8.45 (d, J=2.34 Hz, 1 H) 10.65 (s, 1 H), LCMS Rt=1.73 m/z 351 [MH]+

Workup

  1. waitThe mixture was left
  2. filtrationThe reaction mixture was filtered directly onto a cation exchange cartridge (Bakerbond SCX, sulphonic acid bonded-phase, 1 g)
  3. washThe SCX cartridge was washed with methanol (2×4 ml)
  4. customto remove impurities
  5. customevaporated to an off-white solid
  6. customthat was triturated with isopropanol
  7. filtrationfiltered
  8. washwashed with isopropanol

Sources & evidence

ORD record
ord-6110b537a43e46a1a7b268af1b55db71
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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