Hydrochloric Acid → N-(2-[N-(2-benzyloxy-5-bromobenzyl)-N-ethylamino]pyridine-5-carbonyl)propanesulphonamide

HRID 1455950

Reaktionsgleichung

Reaktionsgleichung von HRID 1455950
[CH2:1]([O:8][C:9]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][C:10]=1[CH2:11][N:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([OH:23])=O)=[CH:17][N:16]=1)[CH2:13][CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:29]([S:32]([NH2:35])(=[O:34])=[O:33])[CH2:30][CH3:31].CN(C1N=CC=CN=1)C.Cl.CN(C)CCCC(N=C=N)C.Cl>ClCCl>[CH2:1]([O:8][C:9]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][C:10]=1[CH2:11][N:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([NH:35][S:32]([CH2:29][CH2:30][CH3:31])(=[O:34])=[O:33])=[O:23])=[CH:17][N:16]=1)[CH2:13][CH3:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 5217172-DimethylaminopyrimidineHCID 3401849Propane-1-sulphonamideHCID 113511902-[N-(5-bromo-2-benzyloxybenzyl)-N-ethylamino]pyridine-5-carboxylic acidHCID 219829211-(3-Dimethylaminopropyl)ethylcarbodiimide hydrochloride

Produkt 1

HCID 22105639N-(2-[N-(2-benzyloxy-5-bromobenzyl)-N-ethylamino]pyridine-5-carbonyl)propanesulphonamideAusbeute 24,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(N-(2-benzyloxy-5-bromobenzyl)-N-ethylamino]pyridine-5-carboxylic acid (0.89 g) in dichloromethane (50 ml) was added propanesulphonamide (0.3 g), dimethylaminopyrimidine (0.493 g) and 1-(3-dimethylaminopropyl)ethylcarbodiimide hydrochloride (0.58 g). The mixture was stirred at ambient temperature for 18 hours, and poured into 2N HCl. The organic layer was separated and washed with water and brine, then dried (MgSO4), filtered and evaporated. The resulting oil was purified by chromatography on silica gel (eluting with 5% ethylacetate/dichloromethane to give N-(2-[N-(2-benzyloxy-5-bromobenzyl)-N-ethylamino]pyridine-5-carbonyl)propanesulphonamide (271 mg) as a white foam.

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting oil was purified by chromatography on silica gel (
  7. washeluting with 5% ethylacetate/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-8c64db4ba7724ab8abb4c242bc02427f
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05843942

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