(r)-Tert-butyl 1-(4-(5-carbamoyl-1h-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-(4-chlorophenyl)-1-oxopropan-2-ylcarbamate → (R)-4-(4-(2-amino-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile

HRID 79519Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 79519
[C:1]([C:4]1[C:5]([N:13]2[CH2:18][CH2:17][N:16]([C:19](=[O:37])[C@H:20]([NH:29]C(=O)OC(C)(C)C)[CH2:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[CH2:15][CH2:14]2)=[C:6]2[CH:12]=[CH:11][NH:10][C:7]2=[N:8][CH:9]=1)(=O)[NH2:2]>O=P(Cl)(Cl)Cl>[NH2:29][C@H:20]([CH2:21][C:22]1[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=1)[C:19]([N:16]1[CH2:17][CH2:18][N:13]([C:5]2[C:4]([C:1]#[N:2])=[CH:9][N:8]=[C:7]3[NH:10][CH:11]=[CH:12][C:6]=23)[CH2:14][CH2:15]1)=[O:37]

Komponenten

3

Edukt 1

HCID 68761929(r)-Tert-butyl 1-(4-(5-carbamoyl-1h-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-(4-chlorophenyl)-1-oxopropan-2-ylcarbamate

Produkt 1

HCID 44198751(R)-4-(4-(2-amino-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrileAusbeute 7,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24813Phosphorus oxychlorideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

(R)-tert-Butyl 1-(4-(5-carbamoyl-1H-pyrrolo[2,3-b]pyri din-4-yl)piperazin-1-yl)-3-(4-chlorophenyl)-1-oxopropan-2-ylcarbamate (0.035 g, 0.066 mmol) was placed in POCl3 (2 mL) and heated to 70° C. for 2 hours. The reaction was then concentrated, diluted with DCM, and washed with saturated NaHCO3. The organic fraction was dried, filtered and concentrated to give a crude residue. The residue was purified (SP4, 12+M, water/CAN 95/5→60/40, 20CV) to give (R)-4-(4-(2-amino-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (0.002 g, 7.4% yield). MS ESI (+) m/z 409 detected.

Aufarbeitung

  1. concentrationThe reaction was then concentrated
  2. additiondiluted with DCM
  3. washwashed with saturated NaHCO3
  4. customThe organic fraction was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude residue
  8. customThe residue was purified (SP4, 12+M, water/CAN 95/5→60/40, 20CV)

Quellen und Nachweise

ORD-Eintrag
ord-674da9d08c5d42b79b70932db553a418
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841304B2

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