Sodium Bicarbonate → 3-fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)-N-(3-oxo-2,2-diphenylpropyl)picolinamide

HRID 1685340Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1685340
[O:1]1CCO[CH:2]1[C:6]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:7][NH:8][C:9](=[O:31])[C:10]1[C:15]([F:16])=[C:14]([S:17][C:18]2[S:22][C:21]([NH:23][C:24]3[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][N:25]=3)=[N:20][CH:19]=2)[CH:13]=[CH:12][N:11]=1.C(=O)(O)[O-].[Na+]>CC(C)=O.O.C1COCC1.Cl>[F:16][C:15]1[C:10]([C:9]([NH:8][CH2:7][C:6]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:2]=[O:1])=[O:31])=[N:11][CH:12]=[CH:13][C:14]=1[S:17][C:18]1[S:22][C:21]([NH:23][C:24]2[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][N:25]=2)=[N:20][CH:19]=1

Komponenten

7

Edukt 2

HCID 516892Sodium BicarbonateHCID 24957734N-(2-(1,3-dioxolan-2-yl)-2,2-diphenylethyl)-3-fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)picolinamide

Produkt 1

HCID 592004433-fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)-N-(3-oxo-2,2-diphenylpropyl)picolinamideAusbeute 104,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 180AcetoneLösungsmittelHCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of N-(2-(1,3-dioxolan-2-yl)-2,2-diphenylethyl)-3-fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)picolinamide (0.248 g, 0.4040 mmol, described in Example 50) in acetone (10 mL), water (5 mL), THF (5 mL) and conc. HCl (1 mL) was heated at gentle reflux for 10 hours. The reaction was then neutralized with aq. sat. sodium bicarbonate and the volatiles were evaporated. The solid was collected by filtration and vacuum dried to give the crude title material (0.240 g, 100%). 1H NMR (400 MHz, DMSO-d6) δ ppm: 2.30 (3H, s), 4.27 (2H, d, J=6.32 Hz), 6.83 (1H, d, J=4.55 Hz), 6.89 (1H, s), 7.03 (1H, t, J=5.31 Hz) 7.22 (4H, d, J=7.07 Hz) 7.31-7.37 (2H, m), 7.40 (4H, t, J=7.33 Hz) 7.77 (1H, s), 8.15 (1H, d, J=5.05 Hz), 8.19 (1H, d, J=5.05 Hz), 8.28 (1H, t, J=6.19 Hz). 9.99 (1H, s) 11.82 (1H, s).

Aufarbeitung

  1. temperatureat gentle reflux for 10 hours
  2. customthe volatiles were evaporated
  3. filtrationThe solid was collected by filtration and vacuum
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-bc717a76aa4b49a99468a1ee7c9e39cd
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148400B2

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