Sodium Hydroxide → HCID 58456138, Verbindung

HRID 410660Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 410660
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:20]2[S:24][C:23]([C@@:25]3([OH:37])[CH2:30][CH2:29][C@H:28]([C:31]([O:33]C)=[O:32])[C:27]([CH3:36])([CH3:35])[CH2:26]3)=[N:22][CH:21]=2)[CH:6]=[C:7]([NH:9][C:10]2[N:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][N:11]=2)[CH:8]=1.[OH-].[Na+]>CO>[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:20]2[S:24][C:23]([C@@:25]3([OH:37])[CH2:30][CH2:29][C@H:28]([C:31]([OH:33])=[O:32])[C:27]([CH3:35])([CH3:36])[CH2:26]3)=[N:22][CH:21]=2)[CH:6]=[C:7]([NH:9][C:10]2[N:15]=[C:14]([C:16]([F:18])([F:19])[F:17])[CH:13]=[CH:12][N:11]=2)[CH:8]=1

Komponenten

4

Edukt 2

HCID 14798Sodium Hydroxide2×HCID 67432750HCID 67432750, Verbindung

Produkt 1

HCID 58456138HCID 58456138, VerbindungAusbeute 36,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A microwave vessel was charged with a solution of the compound of Step 3 (10 mg, 0.019 mmol) in MeOH, and sodium hydroxide (1.0 N in H2O, 56 μl, 0.056 mmol, 3 equiv) was added. The resultant cloudy orange suspension was irradiated in the microwave at 110° C. for 15 min. The reaction was not complete. Additional sodium hydroxide (1.0 N in H2O, 190 uL, 0.19 mmol, 10 eq) was added and the faintly yellow solution was irradiated at 150° C. for 30 min. The reaction mixture was concentrated in vacuo, then partitioned between diethyl ether (75 ml) and water (85 ml). The aqueous layer was acidified with 1N aqueous HCl to pH ˜3-4, then washed with EtOAc (2×35 ml). The combined organic layers were dried over Na2SO4, filtered and concentrated, affording the title compound (3.6 mg, 35%) as an orange oil. MS ESI: [M+H]+ m/z 522.2 1H NMR (500 MHz, DMSO-d6) δ 10.5 (s, 1H), 8.85 (d, J=4.9 Hz, 1H), 8.24 (bs, 1H), 8.14 (s, 1H), 7.93 (s, 1H), 7.65 (s, 1H), 7.46 (s, 1H), 7.33 (d, J=4.9 Hz, 1H), 5.94 (bs, 1H), 4.03-3.99 (m, 3H), 3.14 (m, 2H), 2.19-2.16 (m, 2H), 1.86-1.83 (m, 2H), 1.66-1.60 (m, 2H), 1.17-1.11 (m, 6H). rhSYK activity=+++

Aufarbeitung

  1. additionwas added
  2. customThe resultant cloudy orange suspension was irradiated in the microwave at 110° C. for 15 min
  3. customthe faintly yellow solution was irradiated at 150° C. for 30 min
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. custompartitioned between diethyl ether (75 ml) and water (85 ml)
  6. washwashed with EtOAc (2×35 ml)
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e5288b3f52d54720ad25f338e1138ed9
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759366B2

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