Methanesulfonyl chloride → 4-(4-Amino-6-{4-[4-(4-fluoro-3-methyl-phenyl)-1-(2-methanesulfonyloxy-ethyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidin-5-yl)-pyrazole-1-carboxylic acid tert-butyl ester

HRID 2284058Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2284058
[C:1]([O:5][C:6]([N:8]1[CH:12]=[C:11]([C:13]2[C:14]([NH2:41])=[N:15][CH:16]=[N:17][C:18]=2[N:19]2[CH2:24][CH2:23][CH:22]([C:25]3[N:26]([CH2:38][CH2:39][OH:40])[CH:27]=[C:28]([C:30]4[CH:35]=[CH:34][C:33]([F:36])=[C:32]([CH3:37])[CH:31]=4)[N:29]=3)[CH2:21][CH2:20]2)[CH:10]=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)C(C)C)C.[CH3:51][S:52](Cl)(=[O:54])=[O:53]>C1COCC1>[NH2:41][C:14]1[C:13]([C:11]2[CH:10]=[N:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH:12]=2)=[C:18]([N:19]2[CH2:24][CH2:23][CH:22]([C:25]3[N:26]([CH2:38][CH2:39][O:40][S:52]([CH3:51])(=[O:54])=[O:53])[CH:27]=[C:28]([C:30]4[CH:35]=[CH:34][C:33]([F:36])=[C:32]([CH3:37])[CH:31]=4)[N:29]=3)[CH2:21][CH2:20]2)[N:17]=[CH:16][N:15]=1

Komponenten

5

Edukt 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 894427674-(4-amino-6-{4-[4-(4-fluoro-3-methyl-phenyl)-1-(2-hydroxy-ethyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidin-5-yl)-pyrazole-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 894426624-(4-Amino-6-{4-[4-(4-fluoro-3-methyl-phenyl)-1-(2-methanesulfonyloxy-ethyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidin-5-yl)-pyrazole-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirring solution of 4-(4-amino-6-{4-[4-(4-fluoro-3-methyl-phenyl)-1-(2-hydroxy-ethyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidin-5-yl)-pyrazole-1-carboxylic acid tert-butyl ester (350.00 mg; 0.62 mmol; 1.00 eq.) in THF 5 ml added ethyl-diisopropyl-amine (0.28 ml; 1.56 mmol; 2.50 eq.), then added drop wised methanesulfonyl chloride (0.10 ml; 1.24 mmol; 2.00 eq.) at 0° C., the reaction mixture was stirred at RT for 1 hr, LC-MS showed desired as major, and starting material disappeared, removed off solvent, directly carried the crude product for next step reaction.

Aufarbeitung

  1. customremoved off solvent
  2. customfor next step reaction

Quellen und Nachweise

ORD-Eintrag
ord-5fb19e0d28e144ec90e059b6169ea7bf
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09145392B2

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