Sodium Hydroxide → HCID 86700383, Verbindung

HRID 879559Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 879559
[C:1]([O:5][C@@H:6]([C:12]1[C:36]([CH3:37])=[CH:35][C:15]2[N:16]=[C:17]([C:19]3[N:20]=[C:21]([C:25]4[CH:26]=[C:27]5[C:31](=[CH:32][CH:33]=4)[N:30]([CH3:34])[N:29]=[CH:28]5)[N:22]([CH3:24])[CH:23]=3)[S:18][C:14]=2[C:13]=1[C:38]1[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.O>[C:1]([O:5][C@@H:6]([C:12]1[C:36]([CH3:37])=[CH:35][C:15]2[N:16]=[C:17]([C:19]3[N:20]=[C:21]([C:25]4[CH:26]=[C:27]5[C:31](=[CH:32][CH:33]=4)[N:30]([CH3:34])[N:29]=[CH:28]5)[N:22]([CH3:24])[CH:23]=3)[S:18][C:14]=2[C:13]=1[C:38]1[CH:39]=[CH:40][C:41]([Cl:44])=[CH:42][CH:43]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 86700382HCID 86700382, Verbindung

Produkt 1

HCID 86700383HCID 86700383, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

In a 25 mL round bottom flask, (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-2-(1-methyl-1H-indazol-5-yl)-1H-imidazol-4-yl)benzo[d]thiazol-6-yl)acetate 15 mg, 0.024 mmol) was dissolved in THF (1.5 mL) EtOH (0.7 mL) and water (0.5 mL). Then aqueous NaOH (2 N) (0.4 mL) was added. The reaction mixture was stirred at 30° C. in oil bath for 17 h. The resulting reaction mixture was concentrated. The residue was purified on Gilson reverse phase HPLC with CH3CN and water (10 mL) to afford the product. LCMS-ESI+: calc'd for: C32H30ClN5O3S: 600.2, 602.2, 601.2 (M+H+); Found: 600.3, 602.3, 601.3 (M+H+). 1H NMR (400 MHz, CD3OD) δ 8.03 (d, J=0.8 Hz, 1H), 7.99 (dd, J=1.6, 0.8 Hz, 1H), 7.93-7.88 (m, 1H), 7.83 (s, 1H), 7.67-7.58 (m, 3H), 7.50 (dd, J=8.6, 2.3 Hz, 1H), 7.42 (ddd, J=8.3, 5.5, 2.2 Hz, 2H), 5.01 (s, 1H), 4.03 (d, J=0.7 Hz, 3H), 3.75 (s, 3H), 2.55 (s, 3H), 0.82 (s, 9H).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated
  3. customThe residue was purified on Gilson reverse phase HPLC with CH3CN and water (10 mL)
  4. customto afford the product

Quellen und Nachweise

ORD-Eintrag
ord-7477109aaa9c461d957d423e0b63585e
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987250B2

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