Ammonia → 6-Fluoro-3-((S)-2-methyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridine

HRID 2282541Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2282541
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]2[CH3:18])=O)=[N:6][CH:7]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(CC)CC.ClC(Cl)(Cl)C(Cl)(Cl)Cl.N>C1COCC1.CO.C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:10]([N:12]3[CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]3[CH3:18])=[N:9][N:8]=2)[CH:7]=1

Komponenten

9

Edukt 5

HCID 222AmmoniaHCID 6214HexachloroethaneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 86687104(S)-2-Methyl-piperidine-1-carboxylic acid N'-(5-fluoro-pyridin-2-yl)-hydrazide

Produkt 1

HCID 866871056-Fluoro-3-((S)-2-methyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridineAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of Intermediate 81b (657 mg, 2.60 mmol), Ph3P (1.37 g, 5.21 mmol) and Et3N (1.45 mL, 10.4 mmol) in THF (20 mL) at 0° C. was added hexachloroethane (1.23 g, 5.21 mmol) and the resulting yellow suspension was stirred at RT for 2 h, and at reflux for 19 h. The cooled solution was filtered and concentrated in vacuo. The brown oil was redissolved in MeOH (3 mL) and applied to an SCX-2 cartridge (20 g), washing with MeOH (100 mL). The product was eluted with 2M NH3 in MeOH (75 mL); concentration in vacuo gave a brown oil. FCC, using 1-5% [2M NH3 in MeOH] in DCM, gave the title compound as a brown oil (542 mg, 89%). LCMS (Method 3): Rt 3.00 min, m/z 235 [MH+].

Aufarbeitung

  1. temperatureat reflux for 19 h
  2. filtrationThe cooled solution was filtered
  3. concentrationconcentrated in vacuo
  4. dissolutionThe brown oil was redissolved in MeOH (3 mL)
  5. washwashing with MeOH (100 mL)
  6. washThe product was eluted with 2M NH3 in MeOH (75 mL)
  7. concentrationconcentration in vacuo
  8. customgave a brown oil

Quellen und Nachweise

ORD-Eintrag
ord-6b8f464355224d129d944b99ec956ddd
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139584B2

Notizen zur Reaktion

Wird geladen…