Triethylamine → 2-{[(2S)-1'-{2-[(5R)-3-[3,5-Bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}-N-methyl-N-[3-(methylamino)propyl]acetamide

HRID 446496Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 446496
[F:1][C:2]([F:49])([F:48])[C:3]1[CH:4]=[C:5]([CH:41]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:43]=1)[C:6]([N:8]1[CH2:12][C@@:11]([CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][C:25]3([C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:29][C@@H:28]3[O:36][CH2:37][C:38](O)=[O:39])[CH2:24][CH2:23]2)([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[O:10][CH2:9]1)=[O:7].C([N:52]([CH2:55][CH3:56])[CH2:53]C)C.C(Cl)(=O)C(C)(C)C.[CH3:64][NH:65][CH:66](NC)CC>C(Cl)Cl>[F:49][C:2]([F:48])([F:1])[C:3]1[CH:4]=[C:5]([CH:41]=[C:42]([C:44]([F:46])([F:47])[F:45])[CH:43]=1)[C:6]([N:8]1[CH2:12][C@@:11]([CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][C:25]3([C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:29][C@@H:28]3[O:36][CH2:37][C:38]([N:52]([CH3:53])[CH2:55][CH2:56][CH2:64][NH:65][CH3:66])=[O:39])[CH2:24][CH2:23]2)([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[O:10][CH2:9]1)=[O:7]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 22287041HCID 22287041, VerbindungHCID 86663420{[(2S)-1'-{2-[(5R)-3-[3,5-Bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}acetic acid

Produkt 1

HCID 866634192-{[(2S)-1'-{2-[(5R)-3-[3,5-Bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}-N-methyl-N-[3-(methylamino)propyl]acetamideAusbeute 63,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

The compound (800 mg, 1.15 mmol) obtained in Example 1j was dissolved in methylene chloride (6 mL), triethylamine (0.240 mL, 1.73 mmol) and pivaloyl chloride (0.156 mL, 1.27 mmol) were added under ice cooling, and the mixture was stirred at room temperature for 15 minutes. The reaction mixture was added dropwise to a solution of N,N′-dimethylpropanediamine (588 mg, 5.75 mmol) in methylene chloride (19 mL) under ice cooling, and the mixture was stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure, and the resulting residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=30:1→10:1, v/v) to give the title compound (566 mg; yield, 63%) as a light yellow solid.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. customThe solvent was evaporated under reduced pressure
  3. customthe resulting residue was purified by NH silica gel column chromatography (ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-f4371a52ecb04414be437610027ddff3
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476253B2

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