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

HRID 1162303Notes

Reaction equation

HRID 1162303 reaction equation
[C:1]([N:8](C1C=CC=CC=1)[CH2:9][C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH:19]1[CH:20]=[CH:21][C:22]2N(O)N=N[C:23]=2[CH:24]=1.CCN=C=NCCCN(C)C.Cl.Cl.[CH3:42][C:43]1[N:47]2[C:48](=[O:57])[N:49]([CH:51]3[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]3)[CH2:50][C:46]2=[CH:45][N:44]=1>C(#N)C.C(N(CC)CC)C>[CH3:42][C:43]1[N:47]2[C:48](=[O:57])[N:49]([CH:51]3[CH2:56][CH2:55][N:54]([C:10](=[O:12])[CH:9]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])[C:23]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:24]=4)[CH2:53][CH2:52]3)[CH2:50][C:46]2=[CH:45][N:44]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 21905636N-(tert-Butoxycarbonyl)-N-phenylglycineHCID 230840945-methyl-2-(4-piperidinyl)-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one dihydrochloride

Product 1

HCID 23138346tert-butyl 2-(4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)-2-oxo-1-phenylethylcarbamateYield 95.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

Boc-phenylglycine (0.25 g) was dissolved in acetonitrile (10 ml). HOBt (0.23 g), WSC (0.29 g), triethylamine (0.2 ml) and 5-methyl-2-(4-piperidinyl)-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one dihydrochloride (0.29 g) were added thereto, and mixed at room temperature for 15 hours. The solvent was distilled off under reduced pressure, and the residue was dissolved in ethyl acetate. The ethyl acetate solution was washed with a saturated aqueous sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound as a green oil (0.43 g, 95%).

Workup

  1. additionmixed at room temperature for 15 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe ethyl acetate solution was washed with a saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4ea7662bdb634b32841c130ed1bdf057
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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