Hydrochloric Acid → HCID 86667427, Verbindung

HRID 526997Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 526997
[NH2:1][CH2:2][C@:3]1([OH:18])[CH2:8][CH2:7][CH2:6][C@H:5]([NH:9][C:10]2[C:15]([F:16])=[CH:14][N:13]=[C:12]([Cl:17])[N:11]=2)[CH2:4]1.CCN(C(C)C)C(C)C.[C:28](Cl)(=[O:30])[CH3:29].Cl.[OH-].[Na+]>ClCCl>[Cl:17][C:12]1[N:11]=[C:10]([NH:9][C@H:5]2[CH2:6][CH2:7][CH2:8][C@:3]([CH2:2][NH:1][C:28](=[O:30])[CH3:29])([OH:18])[CH2:4]2)[C:15]([F:16])=[CH:14][N:13]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 86667425(1S,3S)-1-(aminomethyl)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)cyclohexanol2×

Produkt 1

HCID 86667427HCID 86667427, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(1S,3S)-1-(aminomethyl)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)cyclohexanol, 46b, (0.19 g, 0.69 mmol) was dissolved in dichloromethane (15 mL) and treated with DIPEA (1.20 mL, 6.91 mmol) and acetyl chloride (0.10 mL, 1.38 mmol). After 5 minutes, the reaction mixture was diluted into 1N HCl (30 mL), and the aqueous layer was brought to a basic pH by addition of 1N NaOH. The resulting suspension was extracted with dichloromethane (50 mL). The organic layer was dried on Na2SO4 and concentrated in vacuo to provide the crude product, which was purified by silica gel chromatography (20-100% EtOAc/hexanes gradient) to afford 195 mg of N-{[(1S,3S)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)-1-hydroxycyclo-hexyl]methyl}acetamide as a white foamy solid. LCMS RT=2.82 (M+1) 317.33.

Aufarbeitung

  1. extractionThe resulting suspension was extracted with dichloromethane (50 mL)
  2. customThe organic layer was dried on Na2SO4
  3. concentrationconcentrated in vacuo
  4. customto provide the crude product, which
  5. customwas purified by silica gel chromatography (20-100% EtOAc/hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-f6c064fb3d2140638abe22d38d6426fe
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09345708B2

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