Water → 2-{2-[1-(5-Chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethanamine

HRID 1039105

Reaktionsgleichung

Reaktionsgleichung von HRID 1039105
[N:1]([CH2:4][CH2:5][CH:6]1[CH2:8][CH:7]1[CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[N:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=2)[CH2:11][CH2:10]1)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>C1COCC1>[Cl:21][C:18]1[CH:17]=[N:16][C:15]([N:12]2[CH2:13][CH2:14][CH:9]([CH:7]3[CH2:8][CH:6]3[CH2:5][CH2:4][NH2:1])[CH2:10][CH2:11]2)=[N:20][CH:19]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86666146HCID 86666146, Verbindung

Produkt 1

HCID 669270622-{2-[1-(5-Chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethanamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-{4-[2-(2-azidoethyl)cyclopropyl]piperidin-1-yl}-5-chloropyrimidine from step 2 of this example (28 mg, 0,091 mmol) was dissolved in 0.821 mL THF. PPh3 (47.9 mg, 0.182 mmol) was added, followed by addition of 0.091 mL water. The reaction mixture was stirred at room temperature for 1 hour then 40° C. for 3 hours before cooled back to room temperature. The solvent was evaporated in vacuum. The residue was purified by column chromatography eluting with 10% 2M NH3-MeOH/ethyl acetate to give the titled compound. LRMS calc: 280.8; obs: 281.1 (M+1).

Aufarbeitung

  1. temperature40° C. for 3 hours before cooled back to room temperature
  2. customThe solvent was evaporated in vacuum
  3. customThe residue was purified by column chromatography
  4. washeluting with 10% 2M NH3-MeOH/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-7da1855485bb4a1aa25a5360248006ab
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552022B2

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