Hydrochloric Acid → [(Z)-[1-amino-2-[3-[(2-chloro-6H-thieno[2,3-b]pyrrole-5-carbonyl)amino]-2-oxo-3,4-dihydroquinolin-1-yl]ethylidene]amino] ethyl carbonate

HRID 1178443Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1178443
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[NH2:7]/[C:8](=[N:33]\[OH:34])/[CH2:9][N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH:12]([NH:20][C:21]([C:23]2[NH:27][C:26]3[S:28][C:29]([Cl:31])=[CH:30][C:25]=3[CH:24]=2)=[O:22])[C:11]1=[O:32].C1COCC1.Cl>N1C=CC=CC=1.CCOC(C)=O>[NH2:7]/[C:8](=[N:33]\[O:34][C:2]([O:4][CH2:5][CH3:6])=[O:3])/[CH2:9][N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH:12]([NH:20][C:21]([C:23]2[NH:27][C:26]3[S:28][C:29]([Cl:31])=[CH:30][C:25]=3[CH:24]=2)=[O:22])[C:11]1=[O:32]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 10928Ethyl chloroformateHCID 100249933,4-dihydro-2-quinolone (DHQ) derivative, 21

Produkt 1

HCID 21906825[(Z)-[1-amino-2-[3-[(2-chloro-6H-thieno[2,3-b]pyrrole-5-carbonyl)amino]-2-oxo-3,4-dihydroquinolin-1-yl]ethylidene]amino] ethyl carbonate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Ethyl chloroformate (60 μL, 0.63 mmol) was added to a suspension of N-{1-[(2Z)-2-amino-2-(hydroxyimino)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide (Example 31; 200 mg, 0.48 mmol) in dry pyridine (1 mL) under an inert atmosphere then stirred heated to 100° C. for 30 minutes. On cooling THF (10 mL) and added followed by EtOAc (50 mL) and 1M HCl aq. (20 mL). The organic was separated and dried (Na2SO4), filtered and evaporated to give a clear orange oil. This was used in the next stage without characterization or purification.

Aufarbeitung

  1. additionadded
  2. customThe organic was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto give a clear orange oil
  7. customThis was used in the next stage without characterization or purification

Quellen und Nachweise

ORD-Eintrag
ord-fbb5f8ad9d484e77a28a122a08b3e285
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07276517B2

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