Hydrochloric Acid → Hydrochloric Acid

HRID 353260

Reaktionsgleichung

Reaktionsgleichung von HRID 353260
C1CCC(N=C=NC2CCCCC2)CC1.[N+:16]([C:19]1[CH:24]=[C:23]([Cl:25])[C:22](Cl)=[CH:21][C:20]=1[CH2:27][C:28]([N:30]([CH3:49])[C@@H:31]1[C:40]2[C:35](=[CH:36][CH:37]=[C:38]([N+:41]([O-:43])=[O:42])[CH:39]=2)CC[C@H:32]1[N:44]1[CH2:48][CH2:47][CH2:46][CH2:45]1)=[O:29])([O-:18])=[O:17].[N+](C1C=CC=CC=1CC(O)=O)([O-])=O.N1C=CC=CC=1.Cl.O(CC)CC.Cl>>[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:27][C:28]([N:30]([CH3:49])[C@@H:31]([C:40]1[CH:35]=[CH:36][CH:37]=[C:38]([N+:41]([O-:43])=[O:42])[CH:39]=1)[CH2:32][N:44]1[CH2:45][CH2:46][CH2:47][CH2:48]1)=[O:29])([O-:18])=[O:17].[ClH:25]

Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 10868Dicyclohexylcarbodiimide2×HCID 77337(2-Nitrophenyl)acetic acidHCID 10953452Ether hydrochlorideHCID 228794362-(2-Nitro-4,5-dichlorophenyl)-N-methyl-N-[(+/-)-trans-2-(1-pyrrolidinyl)-7-nitro-1,2,3,4-tetrahydronaphth-1-yl]acetamide

Produkt 2

HCID 313Hydrochloric AcidHCID 11774268HCID 11774268, Verbindung

Versuchsvorschrift

This compound was prepared via the general DCC/pyr coupling procedure from 8 (1.4886 g, 5.97 mmol), 2-nitrophenylacetic acid (2.1619 g, 11.93 mmol), DCC(2.5402 g, 12.31 mmol), and pyridine (1.00 mL, 12.36 mmol). The crude product was converted to the HCl salt with Et2O—HCl without chromatography and crystallized from MeOH—Et2O. The first crop was recrystallized again from MeOH—Et2O to yield 10 HCl.(1.3663 g, 51%): m.p. (HCl salt) 258-259° C.; 1H NMR (HCl salt, DMSO-d6) δ1.97 (br s, 4H, —CH2CH2—), 2.91 (s, 3H, —NCH3), 3.11-4.45 (complex, 8H, 4 —CH2—), 6.17 (m, 1H, —CH—), 7.51-8.25 (complex, 8H, aromatic). MS(FAB) m/z 413. Anal. (C, H, N) C21H24N4O5.HCl.0.25H2O.

Aufarbeitung

  1. customcrystallized from MeOH—Et2O
  2. customThe first crop was recrystallized again from MeOH—Et2O

Quellen und Nachweise

ORD-Eintrag
ord-6d1e04bfdd0346869742df3d1ebce36e
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06750216B2

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