Tetrahydrofuran → N-[2-[1-(chloromethyl)-5-nitro-1,2-dihydrobenzo[e]indole-3-carbonyl]-1H-indol-5-yl]acetamide
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Tetrahydrofuran | HCID 8028 | — |
| Edukt | 5-acetamido-1H-indole-2-carboxylic Acid | HCID 10775170 | — |
| Edukt | 3-(tert-butyloxycarbonyl)-1-chloromethyl-5-nitro-1,2-dihydro-3H-benz[e]indole | HCID 15380413 | — |
| Lösungsmittel | Dimethylacetamide | HCID 31374 | — |
| Produkt | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Produkt | N-[2-[1-(chloromethyl)-5-nitro-1,2-dihydrobenzo[e]indole-3-carbonyl]-1H-indol-5-yl]acetamide | HCID 4365483 | 79% |
Reaktionsschritte
Deprotection of 13 (300 mg, 0.83 mmol) as in Example C, and treatment with 5-acetylaminoindole-2-carboxylic acid [M. A. Warpehoski et al., J. Med. Chem. 31, 1988, 590-603] (181 mg, 0.83 mmol) and EDCI.HCl (397 mg, 2.07 mmol) in DMA (3 mL) gave 14c (310 mg, 79%), mp (THF) 252-253° C. 1H NMR [(CD3)2SO] δ 11.77 (d, J=1.2 Hz, 1 H, indole NH), 9.86 (s, 1 H, NHCO), 9.16 (s, 1 H, H-4), 8.35 (dd, J=7.1, 2.6 Hz, 1 H, H-6), 8.24 (dd, J=6.8, 2.5 Hz, 1 H, H-9), 8.10 (d, J=1.3 Hz, H-4'), 7.79-7.70 (m, 2 H, H-7,8), 7.43 (d, J=8.8 Hz, 1 H, H-7'), 7.35 (dd, J=8.8, 1.8 Hz, 1 H, H-6'), 7.27 (d, J=1.8 Hz, 1 H, H-3'), 4.94 (t, J=10.2 Hz, 1 H, H-2), 4.71 (dd, J=11.0, 2.3 Hz, 1 H, H-2), 4.66-4.58 (m, 1 H, H-1), 4.13 (d, J=4.3 Hz, 2 H, CH2Cl), 2.06 (s, 3 H, COCH3).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US06130237 |
| Quelldatensatz | uspto-grants-2000_10 |
| ORD ID | ord-502d11aa9fa94273a604bbd5ecb60bef |
| Quellennotiz | uspto-grants-2000_10 |