Pyridine → Hydrochloric Acid

HRID 353263

Reaktionsgleichung

Reaktionsgleichung von HRID 353263
C1CCC(N=C=NC2CCCCC2)CC1.[N+]([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-])=O.[CH3:50][S:51](C1C=CC(CC(O)=O)=CC=1)(=[O:53])=[O:52].N1C=CC=CC=1>>[CH3:50][S:51]([C:23]1[CH:22]=[CH:21][C:20]([CH2:27][C:28]([N:30]([CH3:49])[C@@H:31]([C:40]2[CH:35]=[CH:36][CH:37]=[C:38]([N+:41]([O-:43])=[O:42])[CH:39]=2)[CH2:32][N:44]2[CH2:48][CH2:47][CH2:46][CH2:45]2)=[O:29])=[CH:19][CH:24]=1)(=[O:53])=[O:52].[ClH:25]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 10868Dicyclohexylcarbodiimide2×HCID 5723454-Mesylphenylacetic acidHCID 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 113852742-(4-Methylsulfonylphenyl)-N-methyl-N-[(1S)-1-(3-nitrophenyl)-2-(1-pyrrolidinyl)ethyl]acetamide

Versuchsvorschrift

This compound was prepared via the general DCC/pyr coupling procedure from 8 (0.5138 g, 2.061 mmol), 4-methylsulfonylphenylacetic acid (0.8825 g, 4.119 mmol), DCC(0.8771 g, 4.251 mmol), and pyridine (0.34 mL, 4.245 mmol). The crude product was gravity column chromatographed eluting with CHCl3:2% NH3 before it was converted to the HCl salt with 1.0 M HCl in Et2O and crystallized from MeOH to yield 14 HCl.(0.4695 g, 47%): m.p. (HCl salt) 276-277° C.; 1H NMR (HCl salt, DMSO-d6) δ2.0 (br s, 4H, —CH2CH2—), 2.92 (s, 3H, —NCH3), 3.2 (s, 3H, —SO2CH3), 3.2-4.3 (complex, 8H, 4 —CH2—), 6.25 (m, 1H, —CH—), 7.61 (d, J=7.2 Hz, 2H, aromatic), 7.75 (m, 2H, aromatic), 7.89 (d, J=7 Hz, 2H, aromatic), 8.12 (s, 1H, aromatic), 8.25 (m, 1H, aromatic). MS(FAB) m/z 446. Anal. (C, H, N) C22H27N3O5S HCl.

Aufarbeitung

  1. customchromatographed
  2. washeluting with CHCl3
  3. customcrystallized from MeOH

Quellen und Nachweise

ORD-Eintrag
ord-fcdaa121866d479688af9d18e13d5a7e
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06750216B2

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