4-Chloro-N-methylbenzenamine → 4-(3-{4-[(4-Chloro-phenyl)-methyl-carbamoyl]-2-fluoro-phenoxy}-propyl)-piperazine-1-carboxylic Acid Tert-butyl Ester

HRID 220907

Reaktionsgleichung

Reaktionsgleichung von HRID 220907
C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][N:35]([CH2:38][CH2:39][CH2:40][O:41][C:42]2[CH:47]=[CH:46][C:45]([C:48]([OH:50])=O)=[CH:44][C:43]=2[F:51])[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].[Cl:52][C:53]1[CH:58]=[CH:57][C:56]([NH:59][CH3:60])=[CH:55][CH:54]=1>ClCCl.CCN(C(C)C)C(C)C>[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][N:35]([CH2:38][CH2:39][CH2:40][O:41][C:42]2[CH:47]=[CH:46][C:45]([C:48](=[O:50])[N:59]([C:56]3[CH:57]=[CH:58][C:53]([Cl:52])=[CH:54][CH:55]=3)[CH3:60])=[CH:44][C:43]=2[F:51])[CH2:34][CH2:33]1)=[O:31])([CH3:27])([CH3:26])[CH3:28]

Komponenten

6

Edukt 3

HCID 702724-Chloro-N-methylbenzenamineHCID 2733179PyBroPHCID 575552094-[3-(4-Carboxy-2-fluoro-phenoxy)-propyl]-piperazine-1-carboxylic Acid Tert-butyl Ester

Produkt 1

HCID 575552734-(3-{4-[(4-Chloro-phenyl)-methyl-carbamoyl]-2-fluoro-phenoxy}-propyl)-piperazine-1-carboxylic Acid Tert-butyl EsterAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 81531DiisopropylethylamineLösungsmittel

Versuchsvorschrift

PyBroP (606 mg, 1.3 mmol) was added to a solution of 4-[3-(4-carboxy-2-fluoro-phenoxy)-propyl]-piperazine-1-carboxylic acid tert-butyl ester from Example E39 (382 mg, 11.0 mmol) in dichloromethane (20 ml) and DIEA (to pH9). The mixture was stirred for 1 h at room temperature then (4-chloro-phenyl)-methyl amine (156 mg, 1.1 mmol) was added. The mixture was stirred for 2 days at room temperature then solvents were concentrated in vacuo. The residue was dissolved in EtOAC, washed with saturated NaHCO3 then brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; EtOAc) to yield the title compound (210 mg, 41%).

Aufarbeitung

  1. stirringThe mixture was stirred for 2 days at room temperature
  2. concentrationsolvents were concentrated in vacuo
  3. dissolutionThe residue was dissolved in EtOAC
  4. washwashed with saturated NaHCO3
  5. dry with materialbrine, dried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel (eluant; EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-59342acd21c4412db3be6a29284765f2
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202858B2

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