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(Diethylamino)sulfur trifluoride → 5-(1-fluorocyclobutyl)-N-[2-(5-methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonylpropan-2-yl]-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridine-2-carboxamide

HRID 1480203
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1480203
O[C:2]1([C:6]2[C:7]([O:28][C@@H:29]([CH3:34])[C:30]([F:33])([F:32])[F:31])=[CH:8][C:9]([C:12]([NH:14][C:15]([C:22]3[N:26]=[C:25]([CH3:27])[O:24][N:23]=3)([CH3:21])[CH2:16][S:17]([CH3:20])(=[O:19])=[O:18])=[O:13])=[N:10][CH:11]=2)[CH2:5][CH2:4][CH2:3]1.CCN(S(F)(F)[F:41])CC>ClCCl>[F:41][C:2]1([C:6]2[C:7]([O:28][C@@H:29]([CH3:34])[C:30]([F:31])([F:32])[F:33])=[CH:8][C:9]([C:12]([NH:14][C:15]([C:22]3[N:26]=[C:25]([CH3:27])[O:24][N:23]=3)([CH3:21])[CH2:16][S:17]([CH3:20])(=[O:18])=[O:19])=[O:13])=[N:10][CH:11]=2)[CH2:3][CH2:4][CH2:5]1
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Komponenten

4

Edukt 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 902034235-(1-hydroxycyclobutyl)-N-[1-methyl-1-(5-methyl-1,2,4-oxadiazol-3-yl)-2-methylsulfonyl-ethyl]-4-[(1S)-2,2,2-trifluoro-1-methyl-ethoxy]pyridine-2-carboxamide

Produkt 1

HCID 902043215-(1-fluorocyclobutyl)-N-[2-(5-methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonylpropan-2-yl]-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridine-2-carboxamideAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 5-(1-hydroxycyclobutyl)-N-[2-(5-methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonylpropan-2-yl]-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridine-2-carboxamide (example 126e, 21 mg, 41.5 μmol) in dry dichloromethane (200 μl) under an argon atmosphere cooled down to 0° C. was added DAST (10.0 mg, 8.22 μl, 62.2 μmol). The reaction mixture was stirred at 0° C. for 1 h and quenched by addition of a 2M aqueous solution of sodium carbonate. The bi-phasic mixture was stirred for 15 minutes and the organic phase was collected. The organic phase was evaporated down to dryness and the crude material was purified by preparative HPLC to yield the title compound (9.2 mg, 44%). MS (ESI, m/z): 509.5 (M+H+).

Aufarbeitung

  1. customquenched by addition of a 2M aqueous solution of sodium carbonate
  2. stirringThe bi-phasic mixture was stirred for 15 minutes
  3. customthe organic phase was collected
  4. customThe organic phase was evaporated down to dryness
  5. customthe crude material was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-6ebcf35676fb46f08d6d1acf35091b32
Quelldatensatz
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09409866B2

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