1,2-Dichloroethane → HCID 24900801, Verbindung

HRID 421651

Reaktionsgleichung

Reaktionsgleichung von HRID 421651
[NH2:1][C:2]1[C:3]([C:15]([NH2:17])=[O:16])=[CH:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[N:14]=1.C(Cl)CCl.[CH2:22]([O:29][CH2:30][C:31](O)=[O:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[NH2:1][C:2]1[C:3]([C:15]([NH2:17])=[O:16])=[CH:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([C:31](=[O:32])[CH2:30][O:29][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:6]=2[N:14]=1

Komponenten

6

Edukt 3

HCID 111,2-DichloroethaneHCID 290301(Benzyloxy)acetic acidHCID 152709842-amino-9H-pyrido[2,3-b]indole-3-carboxamide

Produkt 1

HCID 24900801HCID 24900801, VerbindungAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-9H-pyrido[2,3-b]indole-3-carboxamide (5, 150 mg, 0.663 mmol) in pyridine (7 mL) was added EDC (210 mg, 1.10 mmol), DMAP (85 mg, 0.693 mmol) and benzyloxyacetic acid (142 μL, 0.994 mmol) and the mixture was stirred at RT under an atmosphere of Ar. After 23 h, the reaction was quenched with water (20 mL), poured into a separatory funnel containing EtOAc (100 mL) and washed with water (75 mL). The organic layer was washed with brine (100 mL), dried over sodium sulfate, filtered and concentrated. The crude product was purified by HPLC (Phenomenex Luna 15 μm C18, aqueous HCOOH/CH3CN) to yield 2-amino-9-[(benzyloxy)acetyl]-9H-pyrido[2,3-b]indole-3-carboxamide (28, 54 mg, 22%). NH4OAc standard conditions. DAD Retention time=7.6 min. M+H=375. 1H NMR (300 MHz, DMSO-d6): δ 8.76 (s, 1H), 8.52-8.49 (m, 1H), 8.04 (br s, 1H), 7.83-7.77 (m, 3H), 7.47-7.29 (m, 8H), 5.30 (s, 2H), 4.72 (s, 2H).

Aufarbeitung

  1. customthe reaction was quenched with water (20 mL)
  2. additionpoured into a separatory funnel
  3. additioncontaining EtOAc (100 mL)
  4. washwashed with water (75 mL)
  5. washThe organic layer was washed with brine (100 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by HPLC (Phenomenex Luna 15 μm C18, aqueous HCOOH/CH3CN)

Quellen und Nachweise

ORD-Eintrag
ord-e96ae28fdb5b471d95cc052f2b18a40f
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101604B2

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