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methyl cis-5-amino-1-[4-methyl-6-(1H-pyrazol-5-ylamino)pyrimidin-2-yl]piperidine-3-carboxylate → methyl cis-1-[4-methyl-6-(1H-pyrazol-5-ylamino)pyrimidin-2-yl]-5-[({[(2S)-1,1,1-trifluoropropan-2-yl]oxy}carbonyl)amino]piperidine-3-carboxylate

HRID 383787
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 383787
[NH2:1][C@H:2]1[CH2:7][N:6]([C:8]2[N:13]=[C:12]([CH3:14])[CH:11]=[C:10]([NH:15][C:16]3[NH:20][N:19]=[CH:18][CH:17]=3)[N:9]=2)[CH2:5][C@@H:4]([C:21]([O:23][CH3:24])=[O:22])[CH2:3]1.[C:25](=O)([O:36][C@@H:37]([CH3:42])[C:38]([F:41])([F:40])[F:39])[O:26]C1C=CC([N+]([O-])=O)=CC=1>C(Cl)(Cl)Cl.CCN(C(C)C)C(C)C>[CH3:14][C:12]1[CH:11]=[C:10]([NH:15][C:16]2[NH:20][N:19]=[CH:18][CH:17]=2)[N:9]=[C:8]([N:6]2[CH2:7][C@H:2]([NH:1][C:25]([O:36][C@@H:37]([CH3:42])[C:38]([F:41])([F:40])[F:39])=[O:26])[CH2:3][C@H:4]([C:21]([O:23][CH3:24])=[O:22])[CH2:5]2)[N:13]=1
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Komponenten

5

Edukt 2

HCID 66660299methyl cis-5-amino-1-[4-methyl-6-(1H-pyrazol-5-ylamino)pyrimidin-2-yl]piperidine-3-carboxylateHCID 687562104-nitrophenyl (2S)-1,1,1-trifluoropropan-2-yl carbonate

Produkt 1

HCID 66660365methyl cis-1-[4-methyl-6-(1H-pyrazol-5-ylamino)pyrimidin-2-yl]-5-[({[(2S)-1,1,1-trifluoropropan-2-yl]oxy}carbonyl)amino]piperidine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212
Chloroform
Lösungsmittel
2×
HCID 81531DiisopropylethylamineLösungsmittel

Versuchsvorschrift

The crude methyl cis-5-amino-1-[4-methyl-6-(1H-pyrazol-5-ylamino)pyrimidin-2-yl]piperidine-3-carboxylate prepared in Step 4 of Example 6 was dissolved into CHCl3 (6 ml). To the solution was added the solution of 4-nitrophenyl (2S)-1,1,1-trifluoropropan-2-yl carbonate (203.3 mg) in CHCl3 and DIEA (125.0 μl). After stirring at room temperature for 2 hours, the mixture was concentrated in vacuo. The residue was dissolved into EtOAc, poured into 1 M aqueous solution of NaOH and extracted with EtOAc. The extract was washed with saturated aqueous solution of NaHCO3, dried over MgSO4 and concentrated to give the crude methyl cis-1-[4-methyl-6-(1H-pyrazol-5-ylamino)pyrimidin-2-yl]-5-[({[(2S)-1,1,1-trifluoropropan-2-yl]oxy}carbonyl)amino]piperidine-3-carboxylate as a pale orange amorphous form.

Aufarbeitung

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved into EtOAc
  3. additionpoured into 1 M aqueous solution of NaOH
  4. extractionextracted with EtOAc
  5. washThe extract was washed with saturated aqueous solution of NaHCO3
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b62ddfc14584401a9dc0248dfca81268
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08367690B2

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