1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 58691189, compound

HRID 1392088Notes

Reaction equation

HRID 1392088 reaction equation
[CH2:1]([NH:8][C@H:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:10]=[CH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:18]=[C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21](=[O:28])[N:20]1[C@@H:29]([CH2:33][CH:34]=[CH2:35])[C:30](O)=[O:31].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[CH2:1]([N:8]([C@H:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:10]=[CH2:11])[C:30](=[O:31])[CH:29]([N:20]1[C:21](=[O:28])[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19]1=[O:18])[CH2:33][CH:34]=[CH2:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10998648HCID 10998648, compoundHCID 11139382HCID 11139382, compound

Product 1

HCID 58691189HCID 58691189, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-N-benzyl-1-phenylprop-2-en-1-amine (5a) (240 mg) in DCM (5 mL) at RT under N2 was added (2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)pent-4-enoic acid (4b) (263 mg) and EDAC.HCl (224 mg). The mixture was stirred overnight at RT, then diluted with 30% hexanes/EtOAc and washed with H2O, 0.2 N HCl, saturated NaHCO3, brine, dried (Na2SO4), filtered, and concentrated to a white foamy solid (233 mg, 48%). 1H NMR (300 MHz) The NMR of this compound in both CDCl3 and DMSO-d6 (with elavated temperatures) was complex, thus limiting interpretation. MS APCI, m/z=451 (M+1). LC/MS 3.13 min., Method A.

Workup

  1. washwashed with H2O, 0.2 N HCl, saturated NaHCO3, brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated to a white foamy solid (233 mg, 48%)
  5. customLC/MS 3.13 min., Method A

Sources & evidence

ORD record
ord-e430f31aeeec44178837184f6f3be736
Source dataset
uspto-grants-2008_03
Patent number
US07342007B2

Reaction notes

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