1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 25254653, compound

HRID 1013270Notes

Reaction equation

HRID 1013270 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[C:13]([N:15]2[CH:19]=[N:18][N:17]=[N:16]2)[CH:12]=[C:11]([C:20]([OH:22])=O)[CH:10]=1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH2:31][CH2:32][NH2:33])[CH:28]=[CH:29][CH:30]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH2:31][CH2:32][NH:33][C:20]([C:11]2[CH:10]=[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[CH:14]=[C:13]([N:15]3[CH:19]=[N:18][N:17]=[N:16]3)[CH:12]=2)=[O:22])[CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 748663-MethoxyphenethylamineHCID 757711-HydroxybenzotriazoleHCID 57652715HCID 57652715, compound

Product 1

HCID 25254653HCID 25254653, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2′-Methoxy-5-tetrazol-1-yl-biphenyl-3-carboxylic acid 0.9 g, 3 mmol), 2-(3-methoxy-phenyl)-ethylamine (0.5 mL), EDCI (0.6 g), HOBt (0.4 g) were added to methylene chloride (9 mL), and the reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was partitioned between 1N aqueous HCl and EtOAc, and the combined organic layers were washed with water, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (3-20%, 5% NH4OH in MeOH/methylene chloride) to give 1.5 g of 2′-methoxy-5-tetrazol-1-yl-biphenyl-3-carboxylic acid[2-(3-methoxy-phenyl)-ethyl]-amide as a white solid, MS (M+H)=430.

Workup

  1. customThe reaction mixture was partitioned between 1N aqueous HCl and EtOAc
  2. washthe combined organic layers were washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (3-20%, 5% NH4OH in MeOH/methylene chloride)

Sources & evidence

ORD record
ord-838d9ead9a394555ba33d5c43c0d89f0
Source dataset
uspto-grants-2011_07
Patent number
US07981914B2

Reaction notes

Loading…