Sodium Bicarbonate → HCID 69643317, Verbindung

HRID 1628324Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1628324
[NH2:1][C@@H:2]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:3]([NH:5][C:6]1[C:7]([O:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[N:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[CH:13]=2)[CH:11]=1)=[O:4].[S:35]1[CH:39]=[C:38]([CH:40]=O)[N:37]=[CH:36]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>CCOC(C)=O.C(O)(=O)C>[CH3:18][C:14]1[CH:13]=[C:12]([C:10]2[CH:11]=[C:6]([NH:5][C:3](=[O:4])[C@@H:2]([NH:1][CH2:40][C:38]3[N:37]=[CH:36][S:35][CH:39]=3)[CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:7]([O:19][CH2:20][C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])=[N:8][CH:9]=2)[CH:17]=[CH:16][N:15]=1

Komponenten

7

Edukt 4

HCID 516892Sodium BicarbonateHCID 2763214Thiazole-4-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 69643236HCID 69643236, Verbindung

Produkt 1

HCID 69643317HCID 69643317, VerbindungAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a flask with tert-butyl 2-(3-((S)-2-amino-3-phenylpropanamido)-5-(2-methylpyridin-4-yl)pyridin-2-yloxy)acetate (78.J) (58 mg, 0.13 mmol) was added thiazole-4-carbaldehyde (15 mg, 0.13 mmol). Dichloromathane was added as the solvent. Then acetic acid, glacial (8 mL, 0.13 mmol) was added followed by sodium triacetoxyborohydride (80 mg, 0.38 mmol). The reaction was stirred at room temperature for 1 hour and worked up with EtOAc and saturated NaHCO3 solution. Reverse phase HPLC purification afforded compound 78 26 mg (37%). 1H NMR (400 MHz, MeOH) δ ppm 8.78-8.96 (m, 2H) 8.45 (d, J=5.48 Hz, 1H) 8.22 (d, J=2.35 Hz, 1H) 7.57 (s, 1H) 7.49 (dd, J=5.48, 1.56 Hz, 1H) 7.36 (d, J=1.96 Hz, 1H) 7.18-7.31 (m, 5H) 4.90 (d, J=3.13 Hz, 2H) 3.87-3.98 (m, 2H) 3.63 (dd, J=8.61, 5.09 Hz, 1H) 3.19 (dd, J=13.89, 4.89 Hz, 1H) 2.92 (dd, J=14.09, 8.61 Hz, 1H) 2.60 (s, 3H) 1.46 (s, 9H).

Aufarbeitung

  1. additionDichloromathane was added as the solvent
  2. customReverse phase HPLC purification

Quellen und Nachweise

ORD-Eintrag
ord-4fdedb6c6cc64e61bc0318508c49aa45
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785468B2

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