Dichloromethane → Tert-butyl 4-(2-(3-fluorophenyl)nicotinamido)piperidine-1-carboxylate

HRID 602084Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 602084
NC1CC[N:5]([C:8]([O:10]CC2C=CC=CC=2)=[O:9])CC1.CCN=C=N[CH2:23][CH2:24][CH2:25]N(C)C.CN1CC[O:33][CH2:32]C1.C1[CH:37]=[CH:38][C:39]2[N:44](O)N=N[C:40]=2[CH:41]=1.[F:46][C:47]1[CH:48]=[C:49]([C:53]2[CH:61]=[CH:60][C:56](C(O)=O)=[CH:55][N:54]=2)[CH:50]=[CH:51][CH:52]=1.Cl[CH2:63]Cl>CN(C=O)C>[F:46][C:47]1[CH:48]=[C:49]([C:53]2[N:54]=[CH:55][CH:56]=[CH:60][C:61]=2[C:32]([NH:44][CH:39]2[CH2:38][CH2:37][N:5]([C:8]([O:10][C:24]([CH3:23])([CH3:25])[CH3:63])=[O:9])[CH2:41][CH2:40]2)=[O:33])[CH:50]=[CH:51][CH:52]=1

Komponenten

8

Edukt 6

HCID 6344DichloromethaneHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 178466404-Amino-1-N-Cbz-piperidineHCID 247299726-(3-Fluorophenyl)nicotinic acid

Produkt 1

HCID 67267738Tert-butyl 4-(2-(3-fluorophenyl)nicotinamido)piperidine-1-carboxylateAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Benzyl 4-aminopiperidine-1-carboxylate (11 g, 46.9 mmol), EDAC (9.94 g, 51.9 mmol), NMM (20.7 mL, 189 mmol) and HOBt*H2O (7.22 g, 47 mmol) were added to a solution of 6-(3-fluorophenyl)nicotinic acid (10.2 g, 47 mmol) in dichloromethane:DMF (200 mL:2 mL). The reaction mixture was stirred at room temperature for 18 h, evaporated, and chromatographed (silica gel, ethyl acetate-hexane, 2:1). The solvent was evaporated to give tert-butyl 4-(2-(3-fluorophenyl)nicotinamido)piperidine-1-carboxylate (yield 61%, 12.7 g). LC/MS=434 observed, 434.19 expected

Aufarbeitung

  1. customevaporated
  2. customchromatographed (silica gel, ethyl acetate-hexane, 2:1)
  3. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-0d7571103dc14576aa0a2bacab5cf64d
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902373B2

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