Lithium Hydroxide → 2-((R)-1-(1-(2-hydroxyacetyl)piperidin-4-yl)ethylamino)-4-(5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile

HRID 1853475

Reaktionsgleichung

Reaktionsgleichung von HRID 1853475
[OH-].[Li+].[OH:3][CH2:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([C@H:13]([NH:15][C:16]2[N:21]=[C:20]([C:22]3[C:30]4[C:25](=[N:26][CH:27]=[C:28]([C:31]([F:34])([F:33])[F:32])[CH:29]=4)[N:24](S(C4C=CC(C)=CC=4)(=O)=O)[CH:23]=3)[C:19]([C:45]#[N:46])=[CH:18][N:17]=2)[CH3:14])[CH2:9][CH2:8]1)=[O:6]>O1CCCC1>[OH:3][CH2:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([C@H:13]([NH:15][C:16]2[N:21]=[C:20]([C:22]3[C:30]4[C:25](=[N:26][CH:27]=[C:28]([C:31]([F:33])([F:34])[F:32])[CH:29]=4)[NH:24][CH:23]=3)[C:19]([C:45]#[N:46])=[CH:18][N:17]=2)[CH3:14])[CH2:9][CH2:8]1)=[O:6]

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 594146092-((R)-1-(1-(2-hydroxyacetyl)piperidin-4-yl)ethylamino)-4-(1-tosyl-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile

Produkt 1

HCID 574658362-((R)-1-(1-(2-hydroxyacetyl)piperidin-4-yl)ethylamino)-4-(5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrileAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1M solution of lithium hydroxide (382.5 μl, 0.38 mmol) was added to a solution of 2-((R)-1-(1-(2-hydroxyacetyl)piperidin-4-yl)ethylamino)-4-(1-tosyl-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile (80 mg, 0.128 mmol) in tetrahydrofuran (2 mL). The reaction mixture was stirred at room temperature for 1 hour. The crude mixture was concentrated to dryness and redissolved in ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography (ISCO Companion|) to afford the title compound as a white solid (30 mg, 50% yield).

Aufarbeitung

  1. concentrationThe crude mixture was concentrated to dryness
  2. dissolutionredissolved in ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on silica gel by flash column chromatography (ISCO Companion|)

Quellen und Nachweise

ORD-Eintrag
ord-b352a174b95e4607a9fffc3feec1ab00
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962642B2

Verknüpfte Notizen

Wird geladen…