2-n-Propyl-4-(2-aminoethyl)-1-[2'-(t-butoxycarbonyl)biphenyl-4-yl]methylimidazole → Ethyl 2-n-propyl-3-[2'-(t-butoxycarbonyl)biphenyl-4-yl]methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate oxalate

HRID 21864Notes

Reaction equation

HRID 21864 reaction equation
[CH2:1]([C:4]1[N:5]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:15][CH:14]=2)[CH:6]=[C:7]([CH2:9][CH2:10][NH2:11])[N:8]=1)[CH2:2][CH3:3].O.[C:33]([O:37][CH2:38][CH3:39])(=[O:36])[CH:34]=[O:35]>O1CCCC1>[C:33]([OH:37])(=[O:36])[C:34]([OH:26])=[O:35].[CH2:1]([C:4]1[N:5]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])=[CH:15][CH:14]=2)[C:6]2[CH:34]([C:33]([O:37][CH2:38][CH3:39])=[O:36])[NH:11][CH2:10][CH2:9][C:7]=2[N:8]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 199330042-n-Propyl-4-(2-aminoethyl)-1-[2'-(t-butoxycarbonyl)biphenyl-4-yl]methylimidazoleHCID 22414697Ethyl glyoxylate hydrate

Product 1

HCID 19933007Ethyl 2-n-propyl-3-[2'-(t-butoxycarbonyl)biphenyl-4-yl]methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate oxalateYield 119.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 2-n-propyl-4-(2-aminoethyl)-1-[2'-(t-butoxycarbonyl)biphenyl-4-yl]methylimidazole (10.0 g) and tetrahydrofuran (100 ml) is added a solution of ethyl glyoxylate hydrate (2.90 g) in tetrahydrofuran at room temperature. The reaction mixture is stirred overnight, refluxed for 30 minutes, and evaporated. The residue is dissolved in chloroform and the solution is washed with 2% hydrochloric acid solution, a saturated sodium hydrogen carbonate solution and brine. The organic layer is dried and evaporated. The crude product is crystallized with oxalic acid from ethanol-ether to give ethyl 2-n-propyl-3-[2'-(t-butoxycarbonyl)biphenyl-4-yl]methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate oxalate (8.45 g).

Workup

  1. temperaturerefluxed for 30 minutes
  2. customevaporated
  3. dissolutionThe residue is dissolved in chloroform
  4. washthe solution is washed with 2% hydrochloric acid solution
  5. customThe organic layer is dried
  6. customevaporated
  7. customThe crude product is crystallized with oxalic acid from ethanol-ether

Sources & evidence

ORD record
ord-7c7e60dd00ab46daaa7b3f5937c42490
Source dataset
uspto-grants-1995_06
Patent number
US05424316

Reaction notes

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