Hydrochloric Acid → N-[3-(2-Aminoethoxy)-4-methoxyphenyl]-2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carboxamide

HRID 2392684Notes

Reaction equation

HRID 2392684 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[N:12]=[C:11]([CH3:13])[O:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:22])=O)=[CH:16][CH:15]=1.C(OC([NH:30][CH2:31][CH2:32][O:33][C:34]1[CH:35]=[C:36]([CH:38]=[CH:39][C:40]=1[O:41][CH3:42])[NH2:37])=O)(C)(C)C.Cl>CO>[NH2:30][CH2:31][CH2:32][O:33][C:34]1[CH:35]=[C:36]([NH:37][C:20]([C:17]2[CH:16]=[CH:15][C:14]([C:3]3[CH:4]=[CH:5][C:6]([C:8]4[N:12]=[C:11]([CH3:13])[O:10][N:9]=4)=[CH:7][C:2]=3[CH3:1])=[CH:19][CH:18]=2)=[O:22])[CH:38]=[CH:39][C:40]=1[O:41][CH3:42]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 111301684-[2-methyl-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]benzoic AcidHCID 189800893-(2-(t-Butyloxycarbonylamino)ethoxy)-4-methoxyaniline

Product 1

HCID 18980139N-[3-(2-Aminoethoxy)-4-methoxyphenyl]-2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carboxamideYield 19%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carboxylic acid (EP 0533268 A1) was reacted with 3-(2-(t-butyloxycarbonylamino)ethoxy)-4-methoxyaniline (D11) following a procedure similar to that described in Example 1. The product was dissolved in methanol (10 ml), and treated with 3.3M ethereal HCl solution (3 ml) and left to stand at room temperature for 20 hours. After removal of the solvent in vacuo, the residue was dissolved in H2O solid potassium carbonate was added and the mixture extracted with EtOAC (3×). The combined organic extracts were dried and concentrated in vacuo. Flash column chromatography on silica gel eluting with 5% MeOH/CH2Cl2 gave the title compound as a white solid (0.06 g, 19%) mp 150°-153° C.

Workup

  1. waitleft
  2. customAfter removal of the solvent in vacuo
  3. dissolutionthe residue was dissolved in H2O solid potassium carbonate
  4. additionwas added
  5. extractionthe mixture extracted with EtOAC (3×)
  6. customThe combined organic extracts were dried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-17fbc43bbd404f529580b262d71bdedb
Source dataset
uspto-grants-1998_09
Patent number
US05801170

Reaction notes

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