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Fumaric Acid → 2-tert-butyl-4-[(3-methoxypropyl)amino]-N-(2-methylpropyl)-N-[(3S,5R)-5-(morpholin-4-ylcarbonyl)piperidin-3-yl]pyrimidine-5-carboxamide monofumarate

HRID 2192856
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2192856
[C:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[C:8]([C:17]([N:19]([CH2:34][CH:35]([CH3:37])[CH3:36])[C@H:20]2[CH2:25][C@@H:24]([C:26]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[O:27])[CH2:23][NH:22][CH2:21]2)=[O:18])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:38]([OH:45])(=[O:44])/[CH:39]=[CH:40]/[C:41]([OH:43])=[O:42]>C(OCC)(=O)C.CO>[C:38]([OH:45])(=[O:44])/[CH:39]=[CH:40]/[C:41]([OH:43])=[O:42].[C:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[C:8]([C:17]([N:19]([CH2:34][CH:35]([CH3:37])[CH3:36])[C@H:20]2[CH2:25][C@@H:24]([C:26]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[O:27])[CH2:23][NH:22][CH2:21]2)=[O:18])=[CH:7][N:6]=1)([CH3:3])([CH3:4])[CH3:2]
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Komponenten

5

Edukt 2

HCID 444972Fumaric AcidHCID 252424382-~{tert}-Butyl-4-(3-Methoxypropylamino)-~{n}-(2-Methylpropyl)-~{n}-[(3~{s},5~{r})-5-Morpholin-4-Ylcarbonylpiperidin-3-Yl]pyrimidine-5-Carboxamide

Produkt 1

HCID 866492982-tert-butyl-4-[(3-methoxypropyl)amino]-N-(2-methylpropyl)-N-[(3S,5R)-5-(morpholin-4-ylcarbonyl)piperidin-3-yl]pyrimidine-5-carboxamide monofumarateAusbeute 65,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887
Methanol
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

2-tert-Butyl-4-[(3-methoxypropyl)amino]-N-(2-methylpropyl)-N-[(3S,5R)-5-(morpholin-4-ylcarbonyl)piperidin-3-yl]pyrimidine-5-carboxamide (5.22 g) was dissolved in ethyl acetate (80 ml), and a solution of fumaric acid (1.17 g) in methanol (20 ml) was added. The mixture was heated to 70° C., stirred well and filtered. The filtrate was concentrated under reduced pressure, and the obtained white solid (6.40 g) was suspended in ethyl acetate (190 ml), and dissolved by heating to 70° C. Acetonitrile (190 ml) heated to 70° C. was added, and the mixture was allowed to cool to 50° C. Seed crystals (10 mg) were added, and the mixture was allowed to cool to room temperature with stirring. The mixture was further stirred at 0° C. for 2 hr, and the precipitated white solid was collected by filtration, and washed with ethyl acetate-acetonitrile (1:1). The obtained white crystals were dried under reduced pressure at 100° C. for 12 hr to give the object compound (4.16 g).

Aufarbeitung

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. dissolutiondissolved
  4. temperatureby heating to 70° C
  5. temperatureAcetonitrile (190 ml) heated to 70° C.
  6. additionwas added
  7. temperatureto cool to 50° C
  8. additionSeed crystals (10 mg) were added
  9. temperatureto cool to room temperature
  10. stirringwith stirring
  11. stirringThe mixture was further stirred at 0° C. for 2 hr
  12. filtrationthe precipitated white solid was collected by filtration
  13. washwashed with ethyl acetate-acetonitrile (1:1)
  14. customThe obtained white crystals were dried under reduced pressure at 100° C. for 12 hr

Quellen und Nachweise

ORD-Eintrag
ord-125a988a6e4649df875e8498b8880c31
Quelldatensatz
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08329691B2

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