tert-Butanol → HCID 59013877, Verbindung

HRID 907544

Reaktionsgleichung

Reaktionsgleichung von HRID 907544
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[C:26](Cl)=[N:25][S:24][N:23]=3)[CH2:18][CH2:17]2)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH3:30][N:31]([CH3:40])[C:32]1[CH:33]=[C:34]([CH2:38][OH:39])[CH:35]=[CH:36][CH:37]=1.C(C(CCC)[O-])(C)(C)C.[K+].C(O)(C)(C)C>>[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[C:26]([O:39][CH2:38][C:34]4[CH:35]=[CH:36][CH:37]=[C:32]([N:31]([CH3:40])[CH3:30])[CH:33]=4)=[N:25][S:24][N:23]=3)[CH2:18][CH2:17]2)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Komponenten

5

Edukt 4

HCID 6386tert-ButanolHCID 90133m-(Dimethylamino)benzyl alcoholHCID 23710422HCID 23710422, VerbindungHCID 59013796HCID 59013796, Verbindung

Produkt 1

HCID 59013877HCID 59013877, VerbindungAusbeute 55 %

Versuchsvorschrift

To a round bottom flask equipped with a magnetic stir bar was added 4-(4-Chloro-[1,2,5]thiadiazol-3-yl)-piperazine-1-carboxylic acid (3,5-bis-trifluoromethyl-phenyl)-amide (0.1 g, 0.21 mmol, 1.0 eq.), (3-Dimethylamino-phenyl)-methanol (0.065 g, 0.062 mL, 0.43 mmol, 2.0 eq) and 1M potassium tert-butyl butoxide in t-butanol (0.65 ml, 0.65 mmol, 3.0 eq). The mixture was stirred at room temperature overnight. After removal of solvent in vacuo, the crude mixture was purified on preparative HPLC, affording the title compound N-[3,5-bis(trifluoromethyl)phenyl]-4-[4-({[3-(dimethylamino)phenyl]methyl}oxy)-1,2,5-thiadiazol-3-yl]piperazine-1-carboxamide as a white solid (0.06 g, 55% yield). 1H NMR (DMSO-d6) 9.23 (s, 1H), 8.18 (s, 2H), 7.59 (s, 1H), 7.22 (m, 1H), 6.89 (s, 1H), 6.78 (m, 2H), 5.39 (m, 4H), 3.61 (m, 4H), 3.53 (m, 4H), 2.92 (s, 6H) ppm.

Aufarbeitung

  1. customTo a round bottom flask equipped with a magnetic stir bar
  2. customAfter removal of solvent in vacuo
  3. customthe crude mixture was purified on preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-4dba1c719cd946d5a16932574d7689b4
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08013156B2

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