Ethylmorpholine → 4-Chloro-7-[(1,1-dioxido-4-thiomorpholinyl)carbonyl]-1-methyl-1H-pyrrolo[3,2-c]pyridine

HRID 733726Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 733726
[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][N:10]([CH3:11])[C:6]=2[C:5]([C:12]([OH:14])=O)=[CH:4][N:3]=1.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N1CCOCC1)C.Cl.[NH:45]1[CH2:50][CH2:49][S:48](=[O:52])(=[O:51])[CH2:47][CH2:46]1>CN(C)C=O.O>[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][N:10]([CH3:11])[C:6]=2[C:5]([C:12]([N:45]2[CH2:50][CH2:49][S:48](=[O:52])(=[O:51])[CH2:47][CH2:46]2)=[O:14])=[CH:4][N:3]=1

Komponenten

8

Edukt 5

HCID 7525EthylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 12324096Thiomorpholine 1,1-dioxide hydrochlorideHCID 578409034-Chloro-1-methyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylic acid

Produkt 1

HCID 578409984-Chloro-7-[(1,1-dioxido-4-thiomorpholinyl)carbonyl]-1-methyl-1H-pyrrolo[3,2-c]pyridineAusbeute 80,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-chloro-1-methyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylic acid (726 mg) in dimethylformamide (12 ml) was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (0.73 g), 1-hydroxybenzotriazole (0.52 g), N-ethylmorpholine (0.48 ml) and thiomorpholine 1,1-dioxide hydrochloride (0.66 g). The solution was stirred at room temperature overnight. The reaction was diluted with water and extracted three times with ethyl acetate. The ethyl acetate layers were combined, washed with saturated sodium chloride solution and dried (MgSO4) then evaporated. The residue was triturated with diethyl ether/n-hexane and filtered to afford the title compound as an off-white solid (0.907 g).

Aufarbeitung

  1. extractionextracted three times with ethyl acetate
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. customthen evaporated
  5. customThe residue was triturated with diethyl ether/n-hexane
  6. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-8569668736d3408f894c12450a0682af
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07589206B2

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