3-Methoxycinnamic Acid → 1-(chloromethyl)-3-[(E)-3-methoxycinnamoyl]-5-nitro-1,2-dihydro-3H-benz[e]indole

HRID 366828Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 366828
C(O[C:6]([N:8]1[C:16]2[CH:15]=[C:14]([N+:17]([O-:19])=[O:18])[C:13]3[CH:20]=[CH:21][CH:22]=[CH:23][C:12]=3[C:11]=2[CH:10]([CH2:24][Cl:25])[CH2:9]1)=[O:7])(C)(C)C.CCN=C=NCCCN(C)C.Cl.[CH3:38][O:39][C:40]1[CH:41]=[C:42]([CH:48]=[CH:49][CH:50]=1)/[CH:43]=[CH:44]/C(O)=O>CC(N(C)C)=O>[Cl:25][CH2:24][CH:10]1[C:11]2[C:12]3[CH:23]=[CH:22][CH:21]=[CH:20][C:13]=3[C:14]([N+:17]([O-:19])=[O:18])=[CH:15][C:16]=2[N:8]([C:6](=[O:7])/[CH:44]=[CH:43]/[C:42]2[CH:48]=[CH:49][CH:50]=[C:40]([O:39][CH3:38])[CH:41]=2)[CH2:9]1

Komponenten

5

Edukt 3

HCID 6376683-Methoxycinnamic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 153804133-(tert-butyloxycarbonyl)-1-chloromethyl-5-nitro-1,2-dihydro-3H-benz[e]indole

Produkt 1

HCID 100252921-(chloromethyl)-3-[(E)-3-methoxycinnamoyl]-5-nitro-1,2-dihydro-3H-benz[e]indoleAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

Deprotection of 13 (250 mg, 0.69 mmol) as in Example C above, and reaction of the product with EDCI.HCl (331 mg, 1.73 mmol), (E)-3-methoxycinnamic acid (129 mg, 0.72 mmol) and DMA (3 mL) at 20° C. for 3 h, followed by addition of dilute KHCO3, gave a solid. This was recrystallised from CH2Cl2 /i-Pr2O followed by EtOAc to give 14l (215 mg, 74%), mp 200° C. 1H NMR [(CD3)2SO] δ 9.22 (s, 1 H, H-4), 8.33 (dd, J=7.9, 1.8 Hz, 1 H, H-6), 8.19 (dd, J=7.5, 1.7 Hz, 1 H, H-9), 7.78-7.68 (m, 2 H, H-7,8), 7.72 (d, J=15.4 Hz, 1 H, PhCH=CH), 7.45-7.34 (m, 2 H, H-5',6'), 7.39 (s, 1 H, H-2'), 7.26 (d, J=15.4 Hz, 1 H, PhCH=CH), 7.02 (dt, J=7.2, 2.2 Hz), 1 H, H-4'), 4.71-4.56 (m, 3 H, H-1,2), 4.11-4.05 (m, 2 H, CH2Cl), 3.84 (s, 3 H, CH3). Anal. Calculated for C23H19ClN2O4 : C, 65.3; H, 4.5; N, 6.6; Cl, 8.4. Found: C, 65.0; H, 4.6; N, 6.6; Cl, 8.5%.

Aufarbeitung

  1. customgave a solid
  2. customThis was recrystallised from CH2Cl2 /i-Pr2O

Quellen und Nachweise

ORD-Eintrag
ord-a0aef7f9e2d54f47a6a9a15515425a05
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06130237

Notizen zur Reaktion

Wird geladen…