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

HRID 431720노트

반응식

HRID 431720 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

HCID 230227Pentanediamide수율 395.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9a269a48242c4552b8cc05f98d8f924a
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660742B2

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