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1,8-Diazabicyclo(5.4.0)undec-7-ene → methyl 2-((1R,3S)-3-(5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-ylamino)cyclohexylamino)oxazole-4-carboxylate

HRID 75042
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 75042
[F:1][C:2]1[C:3]([NH:28][C@H:29]2[CH2:34][CH2:33][CH2:32][C@@H:31]([NH2:35])[CH2:30]2)=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[N:10]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:9]=2)=[N:6][CH:7]=1.FC1C=CC(C2C3C(=NC=C(F)C=3)NC=2)=CC=1N[C@H]1CCC[C@@H](N)C1.Cl[C:62]1[O:63][CH:64]=[C:65]([C:67]([O:69][CH3:70])=[O:68])[N:66]=1.C1CCN2C(=NCCC2)CC1>CN(C=O)C.CCOC(C)=O.O>[F:1][C:2]1[C:3]([NH:28][C@H:29]2[CH2:34][CH2:33][CH2:32][C@@H:31]([NH:35][C:62]3[O:63][CH:64]=[C:65]([C:67]([O:69][CH3:70])=[O:68])[N:66]=3)[CH2:30]2)=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[N:10]([S:18]([C:21]3[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=3)(=[O:19])=[O:20])[CH:9]=2)=[N:6][CH:7]=1
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Komponenten

8

Edukt 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 16427154Methyl 2-chloro-1,3-oxazole-4-carboxylateHCID 68007103(1S,3R)-N1-[5-fluoro-2-[5-fluoro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]cyclohexane-1,3-diamineHCID 68007687(1S,3R)-N1-(2-fluoro-5-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)phenyl)cyclohexane-1,3-diamine

Produkt 1

HCID 68007726
methyl 2-((1R,3S)-3-(5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-ylamino)cyclohexylamino)oxazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (1S,3R)—N1-[5-fluoro-2-[5-fluoro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]cyclohexane-1,3-diamine, 44e, (0.089 g, 0.178 mmol) in DMF (1.5 mL) was added methyl 2-chlorooxazole-4-carboxylate (0.031 g, 0.195 mmol), followed by DBU (0.029 mL, 0.195 mmol). The reaction mixture was allowed to stir at room temperature overnight. The reaction was warmed to 75° C. and allowed to stir for 3 hours. Added an additional 16 mg of the chlorooxazole ester and the reaction was heated at 75° C. overnight. The mixture was diluted into water and EtOAc. The layers were separated and the organic phase was washed with brine, dried over MgSO4, filtered and evaporated to dryness. The crude residue was purified by silica gel chromatography (0-20% MeOH/CH2Cl2) to afford 28 mg of desired product: LCMS RT=3.73 (M+1) 624.12.

Aufarbeitung

  1. temperatureThe reaction was warmed to 75° C.
  2. stirringto stir for 3 hours
  3. temperaturethe reaction was heated at 75° C. overnight
  4. customThe layers were separated
  5. washthe organic phase was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe crude residue was purified by silica gel chromatography (0-20% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-2ff58f8333b24e73b031caae05cdcc3c
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08829007B2

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