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Sodium Iodide → 4-({[(1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide

HRID 1360193
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1360193
[CH3:1][C:2]1([CH3:11])[C@H:7]2[CH2:8][C@@H:3]1[CH2:4][CH2:5][C@H:6]2[CH2:9][NH2:10].Cl[C:13]1[C:18]([C:19]([NH2:21])=[O:20])=[CH:17][N:16]=[C:15]2[NH:22][CH:23]=[CH:24][C:14]=12.[I-].[Na+].CN(C)C=O>CN1CCCC1=O.C(N(CC)CC)C.O>[CH3:1][C:2]1([CH3:11])[C@H:7]2[CH2:8][C@@H:3]1[CH2:4][CH2:5][C@H:6]2[CH2:9][NH:10][C:13]1[C:18]([C:19]([NH2:21])=[O:20])=[CH:17][N:16]=[C:15]2[NH:22][CH:23]=[CH:24][C:14]=12
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 11194443Myrtanylamine, cis-(-)-HCID 669241774-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxamide

Produkt 1

HCID 669234214-({[(1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1H-pyrrolo[2,3-b]pyridine-5-carboxamideAusbeute 53,8 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 962WaterLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

To 1-[(1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methaneamine (61 mg) were added a solution of 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (39 mg) in 1-methyl-2-pyrrolidone (0.6 ml), triethylamine (0.056 ml), and sodium iodide (3 mg), and the mixture was stirred at 130° C. for 17 hours. After the reaction mixture was left to cool, to the reaction mixture were added N,N-dimethylformamide (0.3 ml) and water (0.1 ml), and the reaction mixture was dissolved. The reaction mixture was directly purified by preparative HPLC (101M-NH4HCO3+NH3 (pH=9.2):CH3CN=98:2 to 30:70). The active fraction was concentrated and dried to hardness to obtain 4-({[(1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (33.5 mg) as a solid.

Aufarbeitung

  1. waitAfter the reaction mixture was left
  2. temperatureto cool, to the reaction mixture
  3. dissolutionthe reaction mixture was dissolved
  4. customThe reaction mixture was directly purified by preparative HPLC (101M-NH4HCO3+NH3 (pH=9.2):CH3CN=98:2 to 30:70)
  5. concentrationThe active fraction was concentrated
  6. customdried to hardness

Quellen und Nachweise

ORD-Eintrag
ord-0ffe5c77e5a444b2875ab9dd2e75e92f
Quelldatensatz
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07879844B2

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