1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 178501478, compound

HRID 2258596Notes

Reaction equation

HRID 2258596 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:32])[C@H:5]([CH2:28][CH2:29][S:30][CH3:31])[NH:6][C:7](=[O:27])[CH2:8][N:9]([CH2:21][C@@H:22]1[CH2:26][CH2:25][CH2:24][NH:23]1)[CH2:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1.Cl.[NH:34]1[CH:38]=[CH:37][N:36]=[C:35]1CC(O)=O.O.[OH:44][C:45]1C2N=NNC=2C=C[CH:46]=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[CH3:2][O:3][C:4](=[O:32])[C@H:5]([CH2:28][CH2:29][S:30][CH3:31])[NH:6][C:7](=[O:27])[CH2:8][N:9]([CH2:21][C@@H:22]1[CH2:26][CH2:25][CH2:24][N:23]1[C:45](=[O:44])[CH2:46][C:37]1[N:36]=[CH:35][NH:34][CH:38]=1)[CH2:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 532309242-(1H-imidazol-2-yl)acetic acid hydrochlorideHCID 67585810N-(pyrrolidin-2(S)-ylmethyl)-N-(1-naphthylmethyl)-glycyl-methionine methyl ester hydrochlorideHCID 178526939HCID 178526939, compound

Product 1

HCID 178501478HCID 178501478, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(pyrrolidin-2(S)-ylmethyl)-N-(1-naphthylmethyl)-glycyl-methionine methyl ester hydrochloride (0.200 g, 0.387 mmol), imidazoleacetic acid hydrochloride (0.094 g, 0.581 mmol), hydroxybenzotriazole hydrate (0.086 g, 0.639 mmol), EDC hydrochloride (0.134 g, 0.697 mmol) and TEA (0.340 mL, 2.44 mmol) were dissolved in dry DMF (4 mL) and stirred under Ar for 3 h. The mixture was concentrated in vacuo and the residue taken up in aq satd NaHCO3 soln and extracted with EtOAc (2×40 mL). The organics were washed with H2O and brine, dried over MgSO4, filtered and the solvent removed in vacuo to give an oil which was chromatographed on silica gel (5:95 MeOH:CH2Cl2) to give the title compound. 1H NMR (CD3OD) δ 8.32 (d, 1H, J=8 Hz), 7.90 (d, 1H, J=8 Hz), 7.83 (d, 1H, J=8 Hz), 7.39-7.62 (m, 5H), 6.92 (br s, 1H), 4.34-4.52 (m, 3H), 3.94 (d, 1H, J=13 Hz), 3.59-3.78 (m, 2H), 3.67 (s, 3H), 3.21-3.56 (m, 6H), 2.93 (dd, 1H, J=4, 13 Hz), 2.51 (dd, 1H, J=9, 13 Hz), 2.02-2.14 (m, 1H), 1.68-2.02 (m, 6H), 1.92 (s, 3H), 1.39-1.52 (m, 1H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionextracted with EtOAc (2×40 mL)
  3. washThe organics were washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customto give an oil which
  8. customwas chromatographed on silica gel (5:95 MeOH:CH2Cl2)

Sources & evidence

ORD record
ord-31f0a5508c7a4322a430913695ab2727
Source dataset
uspto-grants-1997_08
Patent number
US05661161

Reaction notes

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