Trifluoroacetic acid → (3S)-3-amino-1-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperidin-2-one

HRID 57934Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 57934
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[N:13]=[CH:12][C:11]3[CH:14]=[N:15][N:16]([C:17]4[N:22]=[C:21]([N:23]5[CH2:28][CH2:27][CH2:26][C@H:25]([NH:29]C(=O)OC(C)(C)C)[C:24]5=[O:37])[CH:20]=[CH:19][CH:18]=4)[C:10]=3[CH:9]=2)[CH:5]=[N:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:29][C@H:25]1[CH2:26][CH2:27][CH2:28][N:23]([C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([N:16]3[C:10]4[CH:9]=[C:8]([C:6]5[CH:5]=[N:4][CH:3]=[C:2]([CH3:1])[N:7]=5)[N:13]=[CH:12][C:11]=4[CH:14]=[N:15]3)[N:22]=2)[C:24]1=[O:37]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86707119tert-butyl N-[(3S)-1-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-2-oxo-3-piperidyl]carbamate

Produkt 1

HCID 72714481(3S)-3-amino-1-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperidin-2-oneAusbeute 39,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of tert-butyl N-[(3S)-1-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-2-oxo-3-piperidyl]carbamate (140 mg, 0.280 mmol) in dichloromethane 4.0 ml and trifluoroacetic acid (0.80 ml, 10 mmol) was stirred at RT 3 h. The reaction was concentrated and diluted with water then extracted with EtOAc. The aqueous layer was basified with 1M NaOH to pH 10 then extracted with EtOAc. The organic layers was dried with sodium sulfate, filtered, and concentrated in vacuum. The crude product was submitted for reverse phase HPLC to give 225 (44 mg, 39% yield). MS (ESI) m/z: 401.1. 1H NMR (400 MHz, DMSO) δ 9.60 (s, 1H), 9.47 (s, 1H), 9.33 (s, 1H), 8.72 (s, 1H), 8.64 (s, 1H), 8.05 (t, J=8.1 Hz, 1H), 7.82 (d, J=8.0 Hz, 1H), 7.74 (d, J=8.1 Hz, 1H), 4.46-4.33 (m, 1H), 4.14-4.02 (m, 1H), 3.58 (dd, J=10.8, 6.4 Hz, 1H), 2.65 (s, 3H), 2.24 (dt, J=11.4, 5.3 Hz, 1H), 2.19-2.00 (m, 2H), 1.77 (ddd, J=23.0, 10.6, 5.1 Hz, 1H).

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. additiondiluted with water
  3. extractionthen extracted with EtOAc
  4. extractionthen extracted with EtOAc
  5. dry with materialThe organic layers was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-faccf07d6c8a40169f83e72ba6a327c5
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434725B2

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