Dimethylacetamide → 1-(chloromethyl)-5-nitro-3-[(5-nitroindol-2-yl)carbonyl]-1,2-dihydro-3H-benz[e]indole

HRID 366806

Reaktionsgleichung

Reaktionsgleichung von HRID 366806
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.[N+:26]([C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[NH:34][C:33](C(O)=O)=[CH:32]2)([O-:28])=[O:27].CCN=C=NCCCN(C)C.Cl.CC(N(C)C)=O>Cl>[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]([C:33]2[NH:34][C:35]3[C:31]([CH:32]=2)=[CH:30][C:29]([N+:26]([O-:28])=[O:27])=[CH:37][CH:36]=3)=[O:7])[CH2:9]1

Komponenten

6

Edukt 4

HCID 31374DimethylacetamideHCID 3512915-Nitroindole-2-carboxylic 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 232899531-(chloromethyl)-5-nitro-3-[(5-nitroindol-2-yl)carbonyl]-1,2-dihydro-3H-benz[e]indoleAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A solution of 13 (280 mg, 0.77 mmol) in HCl-saturated dioxane (10 mL) was stirred at 10° C. for 2 h, then evaporated to dryness under reduced pressure below 30° C. 5-Nitroindole-2-carboxylic acid [S. M. Parmerter, J. Amer. Chem. Soc. 80, 1958, 4621-4625] (167 mg, 0.81 mmol) EDCI.HCl (370 mg, 1.93 mmol) and DMA (3 mL) were then added and the mixture was stirred at 20° C. for 2 h. Addition of dilute KHCO3 precipitated a yellow solid which was collected, washed well with water and recrystallised from THF to give 14b (282 mg, 81%), mp >300° C. 1H NMR [(CD3)2SO] δ 12.56 (s, 1 H, NH), 9.14 (s, 1 H, H-4), 8.74 (d, J=2.2 Hz, 1 H, H-4'), 8.35 (dd, J=7.0, 2.7 Hz, 1 H, H-6), 8.24 (dd, J=6.8, 2.7 Hz, 1 H, H-9), 8.12 (dd, J=9.1, 2.3 Hz, 1 H, H-6'), 7.80-7.72 (m, 2 H, H-7,8), 7.64 (d, J=9.1 Hz, 1 H, H-7'), 758 (s, 1 H, H-3'), 4.96 (t, J=10.1 Hz, 1 H, H-2), 4.71 (dd, J=10.8, 2.3 Hz, 1 H, H-2), 4.68-4.61 (m, 1 H, H-1), 4.18-4.09 (m, 2 H, CH2Cl).

Aufarbeitung

  1. customevaporated to dryness under reduced pressure below 30° C
  2. customprecipitated a yellow solid which
  3. customwas collected
  4. washwashed well with water
  5. customrecrystallised from THF

Quellen und Nachweise

ORD-Eintrag
ord-f5357508298d4d258f5e6f1d362d6e30
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06130237

Verknüpfte Notizen

Wird geladen…