Acetic Acid → tert-Butyl (1S,2R)-2-(4-(1-ethyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate

HRID 516056Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 516056
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][C:16]1[CH:25]=[C:24]([C:26]#[N:27])[C:19]([C:20]([O:22]C)=O)=[C:18]([C:28]2[CH:29]=[N:30][N:31]([CH2:33][CH3:34])[CH:32]=2)[N:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(O)=O.C(=O)([O-])[O-].[K+].[K+]>CO.[Pd].C(Cl)Cl>[CH2:33]([N:31]1[CH:32]=[C:28]([C:18]2[C:19]3[C:20](=[O:22])[NH:27][CH2:26][C:24]=3[CH:25]=[C:16]([NH:15][C@@H:10]3[CH2:11][CH2:12][CH2:13][CH2:14][C@@H:9]3[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[N:17]=2)[CH:29]=[N:30]1)[CH3:34]

Komponenten

7

Edukt 3

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 67237978Methyl 6-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-4-cyano-2-(1-ethyl-1H-pyrazol-4-yl)nicotinate

Produkt 1

HCID 86654724tert-Butyl (1S,2R)-2-(4-(1-ethyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamateAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a flask containing methyl 6-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexyl-amino)-4-cyano-2-(1-ethyl-1H-pyrazol-4-yl)nicotinate (62 mg, 0.132 mmol) in MeOH (2 mL) was added HOAc (1 mL) to give a yellow solution. Palladium on carbon was added (14.08 mg, 0.132 mmol). The flask was evacuated and filled with H2 three times, after which the mixture was stirred vigorously at RT under a H2 atmosphere overnight. The mixture was filtered through Celite, and the solvent was removed in vacuo to give a residue, which was dissolved in DCM (10 mL) and MeOH (10 mL). Potassium carbonate was added and the mixture was stirred for 5 h. The solids were filtered out and the filtrate concentrated to give the title compound (50 mg, 86%). [M+H] calc'd for C23H32N6O3, 441; found, 441.

Aufarbeitung

  1. customto give a yellow solution
  2. customThe flask was evacuated
  3. additionfilled with H2 three times
  4. filtrationThe mixture was filtered through Celite
  5. customthe solvent was removed in vacuo
  6. customto give a residue, which
  7. stirringthe mixture was stirred for 5 h
  8. filtrationThe solids were filtered out
  9. concentrationthe filtrate concentrated

Quellen und Nachweise

ORD-Eintrag
ord-c39d3124679046809847a0c0b4c2fe9d
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108970B2

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