1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58504102, compound

HRID 2407732Notes

Reaction equation

HRID 2407732 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([C:13]([OH:15])=O)[CH:3]=1.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[NH2:47][CH2:48][CH:49]1[CH2:54][CH2:53][N:52]([C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[CH2:51][CH2:50]1>ClCCl.C(OCC)(=O)C>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([C:13]([NH:47][CH2:48][CH:49]2[CH2:54][CH2:53][N:52]([C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[CH2:51][CH2:50]2)=[O:15])[CH:3]=1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 27960291-Hydroxybenzotriazole hydrateHCID 118464604-Amino-5-cyano-6-ethoxypicolinic acid

Product 1

HCID 58504102HCID 58504102, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-amino-5-cyano-6-ethoxypicolinic acid (193 mg) in dichloromethane (4 mL) was added 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (215 mg), 1-hydroxybenzotriazole hydrate (164 mg), and diisopropylethylamine (813 μL). The mixture was stirred at room temperature for 5 minutes and then tert-butyl 4-(aminomethyl)piperidine-1-carboxylate (200 mg) was added. The reaction mixture was stirred at room temperature for 16 hours. The organic phase was diluted with ethyl acetate, washed with a saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:1) to obtain the title compound (252 mg) having the following physical data.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 16 hours
  2. washwashed with a saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-6ab4d6c629234b34bcb2fb157f8e10ce
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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