1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 58355743, compound

HRID 1184180Notes

Reaction equation

HRID 1184180 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([C:14]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[O:15])[CH2:11][C@H:10]([N:22]([CH2:39][CH:40]([CH3:42])[CH3:41])[C:23]([C:25]2[N:29]([CH2:30][CH2:31][C:32]([OH:34])=O)[C:28]3[CH:35]=[CH:36][CH:37]=[CH:38][C:27]=3[N:26]=2)=[O:24])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH4+].[N:44]1(O)C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[NH2:44][C:32](=[O:34])[CH2:31][CH2:30][N:29]1[C:28]2[CH:35]=[CH:36][CH:37]=[CH:38][C:27]=2[N:26]=[C:25]1[C:23]([N:22]([CH2:39][CH:40]([CH3:41])[CH3:42])[C@H:10]1[CH2:11][C@@H:12]([C:14]([N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)=[O:15])[CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9]1)=[O:24]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220338091-Hydroxybenzotriazole, ammonium saltHCID 58355100HCID 58355100, compound

Product 1

HCID 58355743HCID 58355743, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(2-{[(3S, 5R)-1-(tert-Butoxycarbonyl)-5-(morpholin-4-ylcarbonyl)piperidin-3-yl](2-methylpropyl)carbamoyl}-1H-benzimidazol-1-yl)propanoic acid (215 mg) and 1H-1,2,3-benzotriazol-1-ol ammonium salt (84 mg) were dissolved in DMF (5 ml), WSC.HCl (142 mg) was added and the mixture was stirred at room temperature for 15 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with 10% aqueous citric acid solution and extracted with ethyl acetate. The extract was washed with aqueous sodium bicarbonate and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate was concentrated under reduced pressure to give the object product (199 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with 10% aqueous citric acid solution
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with aqueous sodium bicarbonate and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. washa fraction eluted with ethyl acetate
  8. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-cf2b28c455f54fdeb84d76b6bb10384e
Source dataset
uspto-grants-2014_03
Patent number
US08664380B2

Reaction notes

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