Water → HCID 60198395, Verbindung

HRID 2279471Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2279471
[N+](C1C=CC(C([O:10][C@H:11]([CH3:41])[C@H:12]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[C:31]=2[F:40])[NH:13][C:14]([N:16]2[CH2:25][CH2:24][C:23]3[CH:22]=[N:21][C:20]([NH:26][CH:27]([CH3:29])[CH3:28])=[N:19][C:18]=3[CH2:17]2)=[O:15])=O)=CC=1)([O-])=O.C([O-])([O-])=O.[K+].[K+].O>CO>[F:40][C:31]1[C:32]([C:36]([F:37])([F:38])[F:39])=[CH:33][CH:34]=[CH:35][C:30]=1[C@H:12]([NH:13][C:14]([N:16]1[CH2:25][CH2:24][C:23]2[CH:22]=[N:21][C:20]([NH:26][CH:27]([CH3:29])[CH3:28])=[N:19][C:18]=2[CH2:17]1)=[O:15])[C@H:11]([OH:10])[CH3:41]

Komponenten

5

Edukt 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 86705484HCID 86705484, Verbindung

Produkt 1

HCID 60198395HCID 60198395, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of (1S,2R)-1-(2-fluoro-3-(trifluoromethyl)phenyl)-1-(2-(isopropylamino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine-7-carboxamido)propan-2-yl 4-nitrobenzoate (40 mg, 0.040 mmol) in MeOH (1 mL) was added 2M K2CO3 (40 μL, 0.079 mmol) at RT. The solution was stirred at RT for 30 min. Water was added and reaction was extracted with DCM. The organic layer was concentrated and the resulting residue was purified by reverse phase column chromatography (SP4) eluting with a MeCH/H2O gradient (5 to 95% MeCN). The recovered product was further purified by SiO2 chromatography eluting with a MeOH/EtOAc (1 to 3% MeOH) to afford 0.6 mg (3.3%) of I-19: LCMS (ACPI-pos) m/z 420.3 (M+H)+.

Aufarbeitung

  1. customreaction
  2. extractionwas extracted with DCM
  3. concentrationThe organic layer was concentrated
  4. customthe resulting residue was purified by reverse phase column chromatography (SP4)
  5. washeluting with a MeCH/H2O gradient (5 to 95% MeCN)
  6. customThe recovered product was further purified by SiO2 chromatography
  7. washeluting with a MeOH/EtOAc (1 to 3% MeOH)
  8. customto afford 0.6 mg (3.3%) of I-19

Quellen und Nachweise

ORD-Eintrag
ord-b5b8c0bdfb8b40a09bc2c6f98826748a
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133187B2

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