4-((S)-2-Fluoro-1-methyl-ethyl)-benzenesulfonyl chloride → N-{7-[4-((S)-2-Fluoro-1-methyl-ethyl)-benzenesulfonylamino]-3,4-dihydro-2H-pyrano[3,2-b]pyridin-3-yl}-propionamide

HRID 870372

Reaktionsgleichung

Reaktionsgleichung von HRID 870372
[NH2:1][C:2]1[CH:3]=[C:4]2[O:11][CH2:10][CH:9]([NH:12][C:13](=[O:16])[CH2:14][CH3:15])[CH2:8][C:5]2=[N:6][CH:7]=1.[F:17][CH2:18][C@H:19]([C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1)[CH3:20]>C(Cl)Cl.N1C=CC=CC=1>[F:17][CH2:18][C@H:19]([C:21]1[CH:26]=[CH:25][C:24]([S:27]([NH:1][C:2]2[CH:3]=[C:4]3[O:11][CH2:10][CH:9]([NH:12][C:13](=[O:16])[CH2:14][CH3:15])[CH2:8][C:5]3=[N:6][CH:7]=2)(=[O:29])=[O:28])=[CH:23][CH:22]=1)[CH3:20]

Komponenten

4

Edukt 2

HCID 536286004-((S)-2-Fluoro-1-methyl-ethyl)-benzenesulfonyl chlorideHCID 68912527N-(7-amino-3,4-dihydro-2H-pyrano[3,2-b]pyridin-3-yl)propionamide

Produkt 1

HCID 68916577N-{7-[4-((S)-2-Fluoro-1-methyl-ethyl)-benzenesulfonylamino]-3,4-dihydro-2H-pyrano[3,2-b]pyridin-3-yl}-propionamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21875418Pyridine methylene chlorideLösungsmittel

Versuchsvorschrift

Following the same procedure as described in example 31.5, a portion of crude N-(7-amino-3,4-dihydro-2H-pyrano[3,2-b]pyridin-3-yl)-propionamide (95 mg, 0.43 mmol) in CH2Cl2/pyridine 9/1 (10 ml) was treated with 4-((S)-2-fluoro-1-methyl-ethyl)benzenesulfonyl chloride (132 mg, 0.55 mmol). Purification by flash column chromatography (CH2Cl2:MeOH, 97:3) gave the title compound (100 mg, 55% for step 31.4 and this step) as a gum.

Aufarbeitung

  1. customPurification by flash column chromatography (CH2Cl2:MeOH, 97:3)

Quellen und Nachweise

ORD-Eintrag
ord-c0f532e3a84147a5b3e01792998d92fe
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969552B2

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