Piperidine → HCID 11990801, Verbindung

HRID 562032

Reaktionsgleichung

Reaktionsgleichung von HRID 562032
[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:29]([NH2:31])=[O:30])[CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]=O)[CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2].[NH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH2:1]([S:3]([N:6]1[CH2:7][CH2:8][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:29]([NH2:31])=[O:30])[CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][N:32]5[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]5)[CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:10][CH2:11]1)(=[O:4])=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 577328043-[1-(ethylsulfonyl)-4-piperidinyl]-5-(3-formylphenyl)-1H-indole-7-carboxamide

Produkt 1

HCID 11990801HCID 11990801, VerbindungAusbeute 50,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(3-formylphenyl)-1H-indole-7-carboxamide (15.0 mg, 0.034 mmol) in DCM (2 mL) was added piperidine (4.0 ul, 0.04 mmol). The reaction solution was stirred at ambient temperature for 1 hr prior to addition of NaBH(OAc)3 (23.0 mg, 0.109 mmol). The resulting mixture was stirred overnight at ambient temperature after which time the solvent was removed under reduced pressure. The resulting residue was dissolved in 1.2 mL DMSO and all undissolved solid was filtered off. This DMSO solution of crude product was purified by reverse phase HPLC (H2O/CH3CN, 0.1% TFA 10-90%) to give the title compound (8.8 mg, 50.5%).

Aufarbeitung

  1. stirringThe resulting mixture was stirred overnight at ambient temperature after which time the solvent
  2. customwas removed under reduced pressure
  3. dissolutionThe resulting residue was dissolved in 1.2 mL DMSO
  4. filtrationall undissolved solid was filtered off
  5. customThis DMSO solution of crude product was purified by reverse phase HPLC (H2O/CH3CN, 0.1% TFA 10-90%)

Quellen und Nachweise

ORD-Eintrag
ord-81b5deac3a634227833c68b09c8b8457
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063071B2

Verknüpfte Notizen

Wird geladen…