1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Pentanediamide

HRID 431720Notes

Reaction equation

HRID 431720 reaction equation
C(OC1C=CC(CCCl)=C([NH:18][C:19]([C:21]2[O:22][C:23]3C=CC(N)=C[C:24]=3[CH:25]=2)=[O:20])C=1)C1C=CC=CC=1.CC[N:33]=C=NCCCN(C)C.O.ON1C2C=CC=CC=2N=N1>CN(C=O)C>[CH2:25]([CH2:21][C:19]([NH2:18])=[O:20])[CH2:24][C:23]([NH2:33])=[O:22]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 187614272-(4-Benzyloxy-2-(5-aminobenzofuran-2-carboxamido)phenyl)ethyl chloride

Product 1

HCID 230227PentanediamideYield 395.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the 2-(4-benzyloxy-2-(5-aminobenzofuran-2-carboxamido)phenyl)ethyl chloride (0.243 mmol) was added the N-[(N-BOC-(4-aminobutyl)-N-methylimidazole-4-(N-methylpyrrole-2-carboxamido)-2-carboxamido)]glutaramide monocarboxylic acid (0.133 g, 0.258 mmol), EDCI (0.093 g, 0.486 mmol) and 1-hydroxybenzotriazole hydrate [HOBT] (0.033 g, 0.244 mmol) which was then dissolved in DMF (15 mL). Dissolution was aided by sonication and the suspension stirred under nitrogen at room temperature for two days with the flask covered with foil. At that time, the DMF was removed via kugelrohr apparatus (0.1 mm Hg, 60° C.). The resulting oil was dissolved in CHCl3, washed with water (1×75 mL), then with brine (1×75 mL) and dried over sodium sulfate. It was then filtered and concentrated under reduced pressure to yield the product N-[(N-BOC-(4-aminobutyl)-N-methylimidazole-4-(N-methylpyrrole-2-carboxamido)-2-carboxamido)]-N-[5-(3-benzyloxy-2-(2-chloroethyl)phenyl)benzofuran-2-carboxamido)]glutarodiamide as a brown oil (0.125 g, 51% yield). Rf=0.40 (10% MeOH/CHCl3) IR (Nujol) 3309, 3190, 1685, 1644, 1536, 1260, 1168, 1096, 1014, 809, 723. 1H-NMR (500 MHz, DMSO-d6) 10.24 (s, 1H), 10.21 (s, 1H), 10.04 (s, 1H), 9.83 (s, 1H), 8.19 (d, 1.5, 1H), 7.90 (t, 6.5, 1H), 7.69 (s, 1H), 7.62 (d, 8.5, 1H), 7.55 (dd, 2.0, 8.5, 1H), 7.46 (s, 1H), 7.44 (d, 8.0, 2H), 7.39 (t, 8.0, 2H), 7.33 (t, 8.0, 1H), 7.30 (d, 8.5, 1H), 7.28 (s, 1H), 7.02 (d, 1.5, 1H), 6.94 (dd, 2.0, 8.5, 1H), 6.90 (d, 1.5, 1H), 6.79 (t br, 1H), 5.09 (s, 2H), 3.91 (s, 3H), 3.82 (s, 3H), 3.76 (t, 6.5, 2H), 3.21 (q, 6.5, 2H), 2.98 (t, 6.5, 2H), 2.90 (t, 6.5, 2H), 2.38 (t, 6.5, 2H), 2.32 (t, 6.5, 2H), 1.91 (quintet, 6.5, 2H), 1.45 (quintet, 6.5, 2H), 1.35 (s, 9H).

Workup

  1. dissolutionDissolution
  2. customwas aided by sonication
  3. customAt that time, the DMF was removed via kugelrohr apparatus (0.1 mm Hg, 60° C.)
  4. dissolutionThe resulting oil was dissolved in CHCl3
  5. washwashed with water (1×75 mL)
  6. dry with materialwith brine (1×75 mL) and dried over sodium sulfate
  7. filtrationIt was then filtered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9a269a48242c4552b8cc05f98d8f924a
Source dataset
uspto-grants-2003_12
Patent number
US06660742B2

Reaction notes

Loading…