1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 69211211, compound

HRID 1392102Notes

Reaction equation

HRID 1392102 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C@@H:12]([CH2:16][CH:17]=[CH2:18])[C:13]([OH:15])=O.CCN=C=NCCCN(C)C.Cl.CC1C=CN=C(N)C=1C.[C:40]1([C@@H:46]([NH:49][CH:50]2[CH2:54][CH2:53][CH2:52][CH2:51]2)[CH:47]=[CH2:48])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(Cl)Cl>[CH:50]1([N:49]([C@H:46]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:47]=[CH2:48])[C:13](=[O:15])[C@H:12]([N:3]2[C:4](=[O:11])[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2]2=[O:1])[CH2:16][CH:17]=[CH2:18])[CH2:54][CH2:53][CH2:52][CH2:51]1

Participants

6

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 110078842-Amino-3,4-dimethylpyridineHCID 11139382HCID 11139382, compoundHCID 58691178HCID 58691178, compound

Product 1

HCID 69211211HCID 69211211, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-20 °C

Procedure

To a solution of (2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)pent-4-enoic acid (361 mg), EDAC.HCl (408 mg), and dimethyl aminopyridine (8 mg) in DCM (4 ml) at −20° C. under N2 was added a solution of N-[(1S)-1-phenylprop-2-en-1-yl]cyclopentanamine in DCM (3 ml). The mixture was allowed to stir at −20° C. for 1 hr then RT overnight. The next day the reaction was diluted with DCM and extracted with 0.1 N HCl. The aqueous layer was back extracted with DCM (×2). All organics were combined, dried (Na2SO4), filtered and evaporated. The resulting residue was purified by column chromatography (10% EtAOc/Hexane) to afford a mixture (85:15) (SS:RS) of the title compound and it's diasteromer (2R)-N-cyclopentyl-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N-[(1S)-1-phenylprop-2-en-1-yl]pent-4-enamide (249 mg) as determined by NMR. 1H NMR (300 MHz, d6-DMSO at 110° C.) δ 1.10-2.12 (m, H9), 2.38-3.15 (m, 2H), 4.88-5.21 (m, 4H), 5.30-5.45 (m, 3H), 5.70-5.90 (m, 1H), 6.00-6.18 (m, 1H), 6.21-6.38 (m, 0.17H), 6.95-7.12 (m, 1H), 7.19-7.41 (m, 5H), 7.18-7.95 (m, 4H). MS APCI, m/z=429 (M+1), LC/MS, 3.04 min.

Workup

  1. customRT overnight
  2. extractionextracted with 0.1 N HCl
  3. extractionThe aqueous layer was back extracted with DCM (×2)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe resulting residue was purified by column chromatography (10% EtAOc/Hexane)

Sources & evidence

ORD record
ord-8db1fd2aee4c4f3aa606f22a933dc379
Source dataset
uspto-grants-2008_03
Patent number
US07342007B2

Reaction notes

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