1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 56644521, compound

HRID 526062Notes

Reaction equation

HRID 526062 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]3[N:16]=[C:17]([S:24][C:25]4[CH:26]=[C:27]([NH:31][C:32](=[O:38])OC(C)(C)C)[CH:28]=[CH:29][CH:30]=4)[C:18]4[S:23][CH:22]=[CH:21][C:19]=4[N:20]=3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.Cl.[CH3:40][N:41]([CH3:48])[CH2:42]/[CH:43]=[CH:44]/C(O)=O.Cl.CN(C)CCCN=C=NCC>N1C=CC=CC=1.C(Cl)(Cl)Cl.CC(O)C>[CH3:40][N:41]([CH3:48])[CH2:42]/[CH:43]=[CH:44]/[C:32]([NH:31][C:27]1[CH:28]=[CH:29][CH:30]=[C:25]([S:24][C:17]2[C:18]3[S:23][CH:22]=[CH:21][C:19]=3[N:20]=[C:15]([NH:14][C:11]3[CH:10]=[CH:9][C:8]([N:5]4[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]4)=[CH:13][CH:12]=3)[N:16]=2)[CH:26]=1)=[O:38]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 45358758(2E)-4-(Dimethylamino)-2-butenoic acid hydrochlorideHCID 70653075HCID 70653075, compound

Product 1

HCID 56644521HCID 56644521, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 21906603Chloroform isopropyl alcoholSolvent

Conditions

Temperature
80 °C

Procedure

40 mg (0.09 mmol) of the compound obtained in Step 2 of Example 223 was dissolved in 1.5 mL of pyridine, and 22 mg (0.14 mmol) of (E)-4-(dimethylamino)-2-butenoic acid hydrochloride and 35 mg (0.18 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride were added thereto, and stirred for 30 minutes at 80° C. Upon the completion of the reaction, the resulting mixture was diluted with mixed solvent of chloroform:2-propanol (3:1(v/v)) and washed with saturated saline. The organic layer was separated, dried over anhydrous Na2SO4, and filtered and distilled under a reduced pressure. The resulting residue was separated by column chromatography (dichloromethane:methanol=6:1 (v/v)) to obtain 2 mg of the title compound (yield: 4%).

Workup

  1. customUpon the completion of the reaction
  2. washwashed with saturated saline
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. distillationdistilled under a reduced pressure
  7. customThe resulting residue was separated by column chromatography (dichloromethane:methanol=6:1 (v/v))

Sources & evidence

ORD record
ord-d1aa6535d4f9473a85388d24101d8903
Source dataset
uspto-grants-2016_05
Patent number
US09345719B2

Reaction notes

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