1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl 1-((4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)carbonyl)pentylcarbamate

HRID 1162315Notes

Reaction equation

HRID 1162315 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][CH2:14][CH2:15][CH3:16])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[CH3:40][C:41]1[N:45]2[C:46](=[O:55])[N:47]([CH:49]3[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]3)[CH2:48][C:44]2=[CH:43][N:42]=1.C1CCN2C(=NCCC2)CC1>C(#N)C.C(N(CC)CC)C>[CH3:40][C:41]1[N:45]2[C:46](=[O:55])[N:47]([CH:49]3[CH2:54][CH2:53][N:52]([C:10]([CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:13][CH2:14][CH2:15][CH3:16])=[O:12])[CH2:51][CH2:50]3)[CH2:48][C:44]2=[CH:43][N:42]=1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 3334352-(((Tert-butoxy)carbonyl)amino)hexanoic acidHCID 23084094HCID 23084094, compound

Product 1

HCID 23138327tert-butyl 1-((4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)carbonyl)pentylcarbamateYield 81.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of 2-((tert-butoxycarbonyl)amino)hexanoic acid (0.46 g) obtained in Example 80a), HOBt (0.46 g) and WSC (0.58 g) in acetonitrile (20 ml) was added a solution of 5-methyl-2-(4-piperidinyl)-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one dihydrochloride (0.6 g), DBU (0.6 ml) and triethylamine (0.61 ml) in acetonitrile (20 ml), and mixed for 15 hours. The solvent was distilled off under reduced pressure, and the residue was dissolved in dichloromethane. The dichloromethane solution was washed with an aqueous sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified with basic silica gel column (ethyl acetate/methanol=10/1) to obtain the title compound as colorless powder (0.7 g, 75%).

Workup

  1. additionmixed for 15 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washThe dichloromethane solution was washed with an aqueous sodium hydrogen carbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified with basic silica gel column (ethyl acetate/methanol=10/1)

Sources & evidence

ORD record
ord-6d4679d0c3cf47f1a8f37e2da8b73118
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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