1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59559661, compound

HRID 1177982Notes

Reaction equation

HRID 1177982 reaction equation
CCN(C(C)C)C(C)C.[C:10]([O:14][C:15]([NH:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([OH:22])=O)=[O:16])([CH3:13])([CH3:12])[CH3:11].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[O:48]=[C:49]([N:66]1[CH2:71][CH2:70][NH:69][CH2:68][CH2:67]1)[CH2:50][NH:51][C:52]([C:54]1[CH:59]=[CH:58][C:57]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)=[CH:56][CH:55]=1)=[O:53]>CN(C=O)C.O>[C:10]([O:14][C:15](=[O:16])[NH:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([N:69]1[CH2:68][CH2:67][N:66]([C:49](=[O:48])[CH2:50][NH:51][C:52]([C:54]2[CH:59]=[CH:58][C:57]([C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=3)=[CH:56][CH:55]=2)=[O:53])[CH2:71][CH2:70]1)=[O:22])([CH3:11])([CH3:12])[CH3:13]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 4087778Boc-2-Abz-OHHCID 57855677Biphenyl-4-carboxylicacid (2-oxo-2-piperazin-1-yl-ethyl)-amide

Product 1

HCID 59559661HCID 59559661, compoundYield 50.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (194.78 mg, 0.26 mL, 0.15 mmol) was added to a stirred solution of 2-tert-butoxycarbonylamino-benzoic acid (79.47 mg, 0.33 mmol) in DMF (3 mL). HOBT (49.7 mg, 0.36 mmol) and EDCI (160.5 mg, 0.83 mmol) were then added at room temperature. After 2 minutes, Biphenyl-4-carboxylic acid (2-oxo-2-piperazin-1-yl-ethyl)-amide (130 mg, 0.4 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and the product was extracted with EtOAc and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to get the residue. The obtained residue was purified by column chromatography (using silicagel of 60-120 mesh and 60% EtOAc in Hexane as eluent) to afford 90 mg (49.5% yield) [2-(4-{2-[(Biphenyl-4-carbonyl)-amino]-acetyl}-piperazine-1-carbonyl)-phenyl]-carbamic acid tert-butyl ester

Workup

  1. extractionthe product was extracted with EtOAc
  2. washthe organic layer was washed with brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto get the residue
  6. customThe obtained residue was purified by column chromatography (using silicagel of 60-120 mesh and 60% EtOAc in Hexane as eluent)

Sources & evidence

ORD record
ord-d28eeb54223e4d1481a2e814c2ea41b6
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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