[2-Amino-6-(2-methoxy-ethoxy)-3-nitro-pyridin-4-yl]-benzyl-carbamic acid ethyl ester → 4-amino-1-benzyl-6-(2-methoxyethoxy)-3H-imidazo[4,5-c]pyridin-2-one

HRID 639606Notes

Reaction equation

HRID 639606 reaction equation
C([O:3][C:4](=O)[N:5]([C:13]1[CH:18]=[C:17]([O:19][CH2:20][CH2:21][O:22][CH3:23])[N:16]=[C:15]([NH2:24])[C:14]=1[N+:25]([O-])=O)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C>C(O)C.[Pd]>[NH2:24][C:15]1[C:14]2[NH:25][C:4](=[O:3])[N:5]([CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:13]=2[CH:18]=[C:17]([O:19][CH2:20][CH2:21][O:22][CH3:23])[N:16]=1

Participants

4

Reactant 1

HCID 67456853[2-Amino-6-(2-methoxy-ethoxy)-3-nitro-pyridin-4-yl]-benzyl-carbamic acid ethyl ester

Product 1

HCID 497716494-amino-1-benzyl-6-(2-methoxyethoxy)-3H-imidazo[4,5-c]pyridin-2-oneYield 52.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

[2-Amino-6-(2-methoxy-ethoxy)-3-nitro-pyridin-4-yl]-benzyl-carbamic acid ethyl ester (118 mg) was dissolved in ethanol (5 ml) and 10% Pd on carbon (15 mg) added. The reaction was stirred under a hydrogen atmosphere (50 psi) for 1 h at RT. The reaction mixture was then filtered through a Celite pad and evaporated. The crude was dissolved in glacial acetic acid (2 ml) and transferred to a microwave vial (Biotage, 0.5-2.0 ml). The vial was sealed and heated under microwave irradiation at 100° C. for 5 minutes. The resultant brown mixture was evaporated then solid loaded on silica and columned on Isco Companion on a silica column (4 g, Redisep), eluting with EtOAc:heptane, increasing the gradient linearly from 60:40 to 100% EtOAc over 8 column volumes (CVs) then isocratic at 100% EtOAc for 8 CVs. The desired fractions were combined and evaporated to provide the title compound as a white solid (50 mg).

Workup

  1. filtrationThe reaction mixture was then filtered through a Celite pad
  2. customevaporated
  3. dissolutionThe crude was dissolved in glacial acetic acid (2 ml)
  4. customThe vial was sealed
  5. temperatureheated under microwave irradiation at 100° C. for 5 minutes
  6. customThe resultant brown mixture was evaporated
  7. washeluting with EtOAc
  8. temperatureheptane, increasing the gradient linearly from 60
  9. customevaporated

Sources & evidence

ORD record
ord-c8b3a3fb9b7b416eb2a546dd0f85b1f7
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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