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Hydrochloric Acid → ethyl [2-({2-methyl-3-[methyl(2-thienylsulfonyl)amino]-4H-thieno[3,2-b]pyrrol-5-yl}carbonyl)hydrazino](oxo)acetate

HRID 453591
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 453591
[CH3:1][C:2]1[S:9][C:8]2[CH:7]=[C:6]([C:10](O)=[O:11])[NH:5][C:4]=2[C:3]=1[N:13]([CH3:22])[S:14]([C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)(=[O:16])=[O:15].O.NN.[N:26]1(O)C2C=CC=CC=2N=[N:27]1.Cl.CN(C)CCCN=C=NCC.C(=O)([O-])[OH:49].[Na+].ClC(=O)[CH2:55][C:56]([O:58][CH2:59][CH3:60])=[O:57].Cl>CN(C)C(=O)C.C(#N)C.O1CCCC1>[CH3:1][C:2]1[S:9][C:8]2[CH:7]=[C:6]([C:10]([NH:26][NH:27][C:55](=[O:49])[C:56]([O:58][CH2:59][CH3:60])=[O:57])=[O:11])[NH:5][C:4]=2[C:3]=1[N:13]([CH3:22])[S:14]([C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)(=[O:16])=[O:15]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

11

Edukt 7

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 757711-HydroxybenzotriazoleHCID 118931Ethyl 3-chloro-3-oxopropionateHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride
HCID 59411385
2-methyl-3-[methyl(2-thienylsulfonyl)amino]-4H-thieno[3,2-b]pyrrole-5-carboxylic acid

Produkt 1

HCID 59411379ethyl [2-({2-methyl-3-[methyl(2-thienylsulfonyl)amino]-4H-thieno[3,2-b]pyrrol-5-yl}carbonyl)hydrazino](oxo)acetateAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6342AcetonitrileLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

To a mixture of 2-methyl-3-[methyl(2-thienylsulfonyl)amino]-4H-thieno[3,2-b]pyrrole-5-carboxylic acid (2.0 g), hydrazine monohydrate (2 mL), 1H-1,2,3-benzotriazol-1-ol (920 mg), tetrahydrofuran (20 mL) and acetonitrile (20 mL) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (1.15 g), and the mixture was stirred at room temperature for 30 min. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated to give a colorless oil. The colorless oil was dissolved in N,N-dimethylacetamide (10 mL), and ethyl 3-chloro-3-oxopropanoate (0.67 mL) was added. The reaction mixture was stirred at room temperature for 1 hr, 1N hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. Crystallization from diethyl ether gave ethyl [2-({2-methyl-3-[methyl(2-thienylsulfonyl)amino]-4H-thieno[3,2-b]pyrrol-5-yl}carbonyl)hydrazino](oxo)acetate (1.7 g, yield 65%) as colorless crystals. melting point 135° C.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give a colorless oil
  6. stirringThe reaction mixture was stirred at room temperature for 1 hr
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe ethyl acetate layer was washed with saturated brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated
  11. customCrystallization from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-eb4703cd2e3b43e6b1dc17277c84be55
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08492405B2

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