1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 67960127, compound

HRID 1529366Notes

Reaction equation

HRID 1529366 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17](O)=[O:18])=[CH:14][CH:15]=2)[C:10]([I:20])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC[N:23]=C=NCCCN(C)C.Cl>CN(C=O)C>[C:17]([C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:9]=[C:10]2[I:20])(=[O:18])[NH2:23]

Participants

4

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67958597HCID 67958597, compound

Product 1

HCID 67960127HCID 67960127, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To solution of 1-(tert-butoxycarbonyl)-3-iodo-1H-indole-5-carboxylic acid (1 g, 2.57 mmol) in DMF (10 mL) at 0° C. was added EDC.HCl (741 mg, 3.86 mmol) and HOBT-NH3 complex (825 mg, 5.15 mmol). The reaction mixture was stirred at RT for 3 h and then extracted with DCM (15 mL). The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated to dryness. The crude product was purified by column chromatography to obtain title compound as an off white solid (550 mg, 50%). MS (ESI, Neg. ion) m/z: 286.9 (M+1).

Workup

  1. extractionextracted with DCM (15 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-3083beb5bd8f4233858dadc8edc48182
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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