Dimethylformamide → Pentanediamide

HRID 431719Notes

Reaction equation

HRID 431719 reaction equation
CCN=C=NCCCN(C)C.[OH2:12].ON1[C:18]2[CH:19]=[CH:20]C=C[C:17]=2[N:16]=N1.C[N:24]([CH:26]=[O:27])C>>[CH2:19]([CH2:18][C:17]([NH2:16])=[O:12])[CH2:20][C:26]([NH2:24])=[O:27]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 230227PentanediamideYield 52%

Procedure

To the above amine was added N-[(N-BOC-(4-aminobutyl)-N-methylpyrrole-4-(N-methylpyrrole-2-carboxamido)-2-carboxamido)]glutaramide monocarboxylic acid (0.132 g, 0.256 mmol), EDCI (0.084 g, 0.439 mmol) and 1-hydroxybenzotriazole hydrate [HOBT] (0.030 g, 0.220 mmol) which was then dissolved in DMF (7.5 mL). Dissolution was aided by sonication and the suspension stirred under nitrogen at room temperature for three days with the flask covered with foil. At that time, the DMF was removed via kugelrohr apparatus (0.1 mm Hg, 60° C.). The residue was purified on a silica gel column using a CHCl3 to 7% MeOH/CHCl3 solvent system to give the desired product N-[(N-BOC-(4-aminobutyl)-N-methylpyrrole-4-(N-methylpyrrole-2-carboxamido)-2-carboxamido)]-N-[5-(3-benzyloxy-2-(2-chloroethyl)phenyl)benzofuran-2-carboxamido)]glutarodiamide as a tan solid (0.108 g, 52% yield). Rf=0.08 (5% MeOH/CHCl3). M.p. 80-84° C. 1H-NMR (500 MHz, DMSO-d6) 10.21 (s, 1H), 10.04 (s, 1H), 9.82 (s, 1H), 9.81 (s, 1H), 5.09 (s, 3H), 3.82 (s, 3H), 3.78 (s, 3H). FAB-MS (NBA) 949 (M+H+, 1). FAB-MS (NBA+K+) 987 (M+K+, 1). Accurate mass calculated for C50H57N8O9Cl+Na: calcd. 971.3835, obs. 971.3821.

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. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-141a7a3301fa4f0ebf98d50962bbe96e
Source dataset
uspto-grants-2003_12
Patent number
US06660742B2

Reaction notes

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