Methanesulfonyl chloride → 4-{[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-methanesulfonyl-amino}-piperidine-1-carboxylic acid tert-butyl ester

HRID 2386387

Reaktionsgleichung

Reaktionsgleichung von HRID 2386387
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([Cl:28])[N:23]=3)[CH:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:29][S:30](Cl)(=[O:32])=[O:31]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([Cl:28])[N:23]=3)[CH:17]=2)[S:30]([CH3:29])(=[O:32])=[O:31])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

3

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 866032634-[3-(2-Chloro-pyrimidin-4-yl)-benzylamino]-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 866032644-{[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-methanesulfonyl-amino}-piperidine-1-carboxylic acid tert-butyl ester

Versuchsvorschrift

Intermediate 29 was coupled with methanesulfonyl chloride following procedure D. LC-MS showed the product had the expected M+H+ of 481. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.4 (s, 1H) 8.39 (d, 1H) 8.2 (d, 1H) 7.6 (d, 1H) 7.5 (s, 1H), 7.3 (m, 3H), 7.0 (d, 1H), 6.9 (d 1H), 6.8 (d, 2H), 6.5 (d, 2H), 4.6 (s, 2H), 3.6 (m, 4H), 2.8 (t, 2H), 1.2 (d, 3H).

Quellen und Nachweise

ORD-Eintrag
ord-94b7cefaecfa43fbb438dac60fc551f7
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08268822B2

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