Water → HCID 22349911, compound

HRID 896714Notes

Reaction equation

HRID 896714 reaction equation
[NH2:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([C:18]([O:20][CH3:21])=[O:19])=[C:13]([F:17])[CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[C:22]([O:26][C:27]([NH:29][C:30]1([C:33](O)=[O:34])[CH2:32][CH2:31]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].C1C=CC2N(O)N=NC=2C=1.O.CCN=C=NCCCN(C)C>C(Cl)Cl>[C:22]([O:26][C:27]([NH:29][C:30]1([C:33]([NH:1][C:2]([C:5]2[CH:10]=[CH:9][C:8]([C:11]3[C:12]([C:18]([O:20][CH3:21])=[O:19])=[C:13]([F:17])[CH:14]=[CH:15][CH:16]=3)=[CH:7][CH:6]=2)([CH3:4])[CH3:3])=[O:34])[CH2:32][CH2:31]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]

Participants

7

Reactant 5

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 6883961-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acidHCID 22349880HCID 22349880, compound

Product 1

HCID 22349911HCID 22349911, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The above-mentioned amine (80 mg, 0.28 mmol), was dissolved in anhydrous DCM (4 mL). To this stirred solution was added 1-[(tert-butoxycarbonyl)amino]cyclopropanecarboxylic acid (67 mg, 0.33 mmol), HOBt.H2O (8 mg, 0.08 mmol) and lastly EDCI (69 g, 0.36 mmol). This mixture was allowed to stir overnight. Solvent was then removed under reduced pressure and the residue was subjected to silica gel chromatography eluting with a 1-3% MeOH in DCM gradient to provide methyl 4′-{1-[({1-[(tert-butoxycarbonyl)amino]cyclopropyl}carbonyl)amino]-1-methylethyl}-3-fluoro-1,1′-biphenyl-2-carboxylate (82 mg), giving LC/MS and proton NMR spectra consistent with theory.

Workup

  1. customSolvent was then removed under reduced pressure
  2. washeluting with a 1-3% MeOH in DCM gradient

Sources & evidence

ORD record
ord-028342bd006944f48568b1118375f12c
Source dataset
uspto-grants-2005_07
Patent number
US06919343B2

Reaction notes

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