Chloroform → 7-fluoro-1-(2-{4-[([1,3]oxathiolo[5,4-c]pyridin-6-ylmethyl)amino]-1-piperidinyl}ethyl)-2(1H)-quinolinone Dihydrochloride

HRID 656861

Reaktionsgleichung

Reaktionsgleichung von HRID 656861
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([F:20])[CH:18]=3)[CH:13]=[CH:12][C:11]2=[O:21])[CH2:4][CH2:3]1.[S:22]1[C:30]2[CH:29]=[C:28]([CH:31]=O)[N:27]=[CH:26][C:25]=2[O:24][CH2:23]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(Cl)(Cl)[Cl:48]>CO>[ClH:48].[ClH:48].[F:20][C:17]1[CH:18]=[C:19]2[C:14]([CH:13]=[CH:12][C:11](=[O:21])[N:10]2[CH2:9][CH2:8][N:5]2[CH2:6][CH2:7][CH:2]([NH:1][CH2:31][C:28]3[N:27]=[CH:26][C:25]4[O:24][CH2:23][S:22][C:30]=4[CH:29]=3)[CH2:3][CH2:4]2)=[CH:15][CH:16]=1

Komponenten

6

Edukt 4

HCID 6212ChloroformHCID 5049666Sodium triacetoxyborohydrideHCID 59254367[1,3]Oxathiolo[5,4-c]pyridine-6-carbaldehydeHCID 667744061-[2-(4-Amino-1-piperidinyl)ethyl]-7-fluoro-2(1H)-quinolinone

Produkt 1

HCID 689923617-fluoro-1-(2-{4-[([1,3]oxathiolo[5,4-c]pyridin-6-ylmethyl)amino]-1-piperidinyl}ethyl)-2(1H)-quinolinone Dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 1-[2-(4-amino-1-piperidinyl)ethyl]-7-fluoro-2(1H)-quinolinone (100 mg; 0.364 mmol) and [1,3]oxathiolo[5,4-c]pyridine-6-carbaldehyde (for a synthesis see WO2004058144, Example 61) (57 mg; 0.364 mmol) were dissolved in a 5:1 mixture of chloroform and methanol (5 ml: 1 ml) and stirred at rt under argon for 1 h. The mixture was then treated with NaBH(OAc)3 (231 mg; 1.092 mmol) and stirred for a further 1 h. The solvents were then removed and the crude residues purified by chromatography on silica gel using a 0-15% MeOH/DCM gradient to provide the title compound as free base (140 mg; 92%)

Aufarbeitung

  1. stirringstirred for a further 1 h
  2. customThe solvents were then removed
  3. customthe crude residues purified by chromatography on silica gel using a 0-15% MeOH/DCM gradient

Quellen und Nachweise

ORD-Eintrag
ord-3b81060ee2224583b7e0e7b201b69d69
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071592B2

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