HCID 19932982, compound → HCID 178439974, compound

HRID 1655119Notes

Reaction equation

HRID 1655119 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]3[N:29](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:28]=[N:27][N:26]=3)=[CH:15][CH:14]=2)[CH:6]=[C:7]([CH2:9][CH2:10][NH2:11])[N:8]=1)[CH2:2][CH3:3].O.[C:50]([O:54][CH2:55][CH3:56])(=[O:53])[CH:51]=[O:52].C([OH:59])C.Cl>O1CCCC1>[C:50]([OH:54])(=[O:53])[C:51]([OH:59])=[O:52].[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]3[NH:29][N:28]=[N:27][N:26]=3)=[CH:15][CH:14]=2)[C:6]2[CH:51]([C:50]([O:54][CH2:55][CH3:56])=[O:53])[NH:11][CH2:10][CH2:9][C:7]=2[N:8]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 19932982HCID 19932982, compoundHCID 21887872Ethanol hydrochlorideHCID 22414697Ethyl glyoxylate hydrate

Product 1

HCID 178439974HCID 178439974, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 2-n-propyl-4-(2-aminoethyl)-1-[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl)methylimidazole (21.95 g) and tetrahydrofuran (200 ml) is added a solution of ethyl glyoxylate hydrate (4.25 g) in tetrahydrofuran (20 ml) at 5° C. The mixture is stirred overnight at room temperature and refluxed for 30 minutes. To a mixture is added a 8% hydrogen chloride ethanol solution (100 ml) at room temperature. The reaction mixture is stirred for 30 minutes, then evaporated. The residue is dissolved in chloroform and washed successively with a saturated sodium hydrogen carbonate solution and brine. The organic layer is dried and evaporated. The oxalate is recrystallized from ethanol to give ethyl 2-n-propyl-3-[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate oxalate (10.84 g).

Workup

  1. temperaturerefluxed for 30 minutes
  2. stirringThe reaction mixture is stirred for 30 minutes
  3. customevaporated
  4. dissolutionThe residue is dissolved in chloroform
  5. washwashed successively with a saturated sodium hydrogen carbonate solution and brine
  6. customThe organic layer is dried
  7. customevaporated
  8. customThe oxalate is recrystallized from ethanol

Sources & evidence

ORD record
ord-c9bc6ae52d6348d389c44eb2dddd1309
Source dataset
uspto-grants-1995_04
Patent number
US05409936

Reaction notes

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