Sodium Bicarbonate → 6-(4-{1-[(8R)-8-(Hydroxymethyl)-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepin-3-yl]cyclopropyl}phenyl)nicotinonitrile

HRID 1424095Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1424095
[Si]([O:8][CH2:9][C@:10]1([CH3:37])[S:16][CH2:15][CH2:14][N:13]2[C:17]([C:20]3([C:23]4[CH:28]=[CH:27][C:26]([C:29]5[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][N:30]=5)=[CH:25][CH:24]=4)[CH2:22][CH2:21]3)=[N:18][N:19]=[C:12]2[CH2:11]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)([O-])O.[Na+]>O1CCCC1>[OH:8][CH2:9][C@:10]1([CH3:37])[S:16][CH2:15][CH2:14][N:13]2[C:17]([C:20]3([C:23]4[CH:28]=[CH:27][C:26]([C:29]5[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][N:30]=5)=[CH:25][CH:24]=4)[CH2:22][CH2:21]3)=[N:18][N:19]=[C:12]2[CH2:11]1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 867129436-(4-{1-[(8R)-8-({[t-Butyl(dimethyl)silyl]oxy}methyl)-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepin-3-yl]cyclopropyl}phenyl)nicotinonitrile

Produkt 1

HCID 867129446-(4-{1-[(8R)-8-(Hydroxymethyl)-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepin-3-yl]cyclopropyl}phenyl)nicotinonitrileAusbeute 71,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The compound (375 mg, 0.70 mmol) obtained in Example 61-1) was dissolved in tetrahydrofuran (7 mL). Tetrabutylammonium fluoride (1.0 mol/L tetrahydrofuran solution, 0.84 mL, 0.84 mmol) was added to the solution at room temperature, and the mixture was stirred at room temperature for 1 h under a nitrogen atmosphere. Saturated aqueous sodium hydrogencarbonate (10 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate (50 mL). The organic layer was washed with saturated sodium chloride solution and then dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (elution solvent: methanol/ethyl acetate=10% to 40%) to obtain the title compound (208 mg, 71%) in a white solid form.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate (50 mL)
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried with anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (elution solvent: methanol/ethyl acetate=10% to 40%)

Quellen und Nachweise

ORD-Eintrag
ord-5fba7edd33ee4cb6ae6edcddf7f9aad4
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927536B2

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