Hydroxyamine hydrochloride → 3,4-dihydro-2-quinolone (DHQ) derivative, 21

HRID 1247509Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1247509
Cl.[NH2:2][OH:3].C[O-].[Na+].[Cl:7][C:8]1[S:32][C:11]2[NH:12][C:13]([C:15]([NH:17][CH:18]3[CH2:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]([CH2:28][C:29]#[N:30])[C:19]3=[O:31])=[O:16])=[CH:14][C:10]=2[CH:9]=1>CO.C1COCC1.CCOC(C)=O>[NH2:30]/[C:29](=[N:2]\[OH:3])/[CH2:28][N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:27][CH:18]([NH:17][C:15]([C:13]2[NH:12][C:11]3[S:32][C:8]([Cl:7])=[CH:9][C:10]=3[CH:14]=2)=[O:16])[C:19]1=[O:31]

Komponenten

7

Edukt 3

HCID 443297Hydroxyamine hydrochlorideHCID 104526402-Chloro-N-[1-(cyanomethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamideHCID 10942334Sodium Methoxide

Produkt 1

HCID 100249933,4-dihydro-2-quinolone (DHQ) derivative, 21Ausbeute 101,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Hydroxylamine hydrochloride (181 mg, 2.60 mmol) in MeOH (5 mL) was added to a solution of NaOMe in MeOH (10.20 mL, 0.25M) under an inert atmosphere followed by 2-chloro-N-[1-(cyanomethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide (Example 27; 500 mg, 1.30 mmol) in THF (7 mL) then stirred for 18 hours. The mixture was diluted with EtOAc (100 mL) and washed with brine (25 mL), dried (Na2SO4), filtered and evaporated to afford the title product (550 mg, 100%) as a pale brown solid.

Aufarbeitung

  1. washwashed with brine (25 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-29a74013d9db420f87d9481a6a54a992
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129249B2

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