1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 69686698, compound

HRID 2231072Notes

Reaction equation

HRID 2231072 reaction equation
C(O[C:9](=[O:46])[CH2:10][CH2:11][CH:12]([N:35]1[C:43](=[O:44])[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:36]1=[O:45])[C:13]([N:15]([CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[NH:16]C(OCC1C=CC=CC=1)=O)=[O:14])C1C=CC=CC=1.Cl.CN(C)CCCN=C=NCC>[Pd].O1CCCC1.CN(C=O)C>[C:31]([O:30][C:28](=[O:29])[CH2:27][N:15]1[C:13](=[O:14])[CH:12]([N:35]2[C:36](=[O:45])[C:37]3[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:43]2=[O:44])[CH2:11][CH2:10][C:9](=[O:46])[NH:16]1)([CH3:34])([CH3:32])[CH3:33]

Participants

6

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 54348520HCID 54348520, compound

Product 1

HCID 69686698HCID 69686698, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 5-(N′-benzyloxycarbonyl-N-tert-butoxycarbonylmethyl-hydrazino)-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-oxo-pentanoic acid benzyl ester (3) and 10% palladium on carbon (250 mg) in tetrahydrofuran (THF) (30 mL) and DMF (3 mL) was stirred under hydrogen atmosphere for 16 hours. The mixture was filtered through Celite and the filtrate was evaporated in vacuo. The residue was dissolved in 30 mL of dichloromethane. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (770 mg, 4 mmol) was added and the solution was stirred at room temperature for 3.5 hours. Solvent was removed in vacuo and the residue was dissolved in ethyl acetate (300 mL), then washed with water (100 mL×2). The organic layer was dried over anhydrous Na2SO4, filtered, purified by flash chromatography using hexane/ethyl acetate (85/15 to 50/50) to afford 1.06 g (75% yield) of the title compound. 1H-NMR (500 MHz, CDCl3) δ 1.40 (s, 9H), 2.30-2.40 (m, 1H), 2.40-2.50 (m, 1H), 3.05-3.12 (m, 1H), 3.38-3.48 (m, 1 H), 3.90-4.00 (d, 1H), 4.60-4.70 (d, 1H), 5.55-5.63 (m, 1H), 7.65 (s, 1H), 7.75-7.7.9 (m, 2H), 7.88-7.92 (m, 2H). Analytical HPLC: 10.36 min. LC-MS (ES+): m/e=388 (M+H+).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe filtrate was evaporated in vacuo
  3. dissolutionThe residue was dissolved in 30 mL of dichloromethane
  4. stirringthe solution was stirred at room temperature for 3.5 hours
  5. customSolvent was removed in vacuo
  6. dissolutionthe residue was dissolved in ethyl acetate (300 mL)
  7. washwashed with water (100 mL×2)
  8. dry with materialThe organic layer was dried over anhydrous Na2SO4
  9. filtrationfiltered
  10. custompurified by flash chromatography

Sources & evidence

ORD record
ord-93cea0b4e8e74f999527fa44f15f82ac
Source dataset
uspto-grants-2002_07
Patent number
US06426413B1

Reaction notes

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