Triethylamine → HCID 23582278, Verbindung

HRID 238729

Reaktionsgleichung

Reaktionsgleichung von HRID 238729
[F:1][C:2]1[CH:3]=[C:4]([C@@:15]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)([NH2:23])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:5]=[C:6]([O:8][C:9]([F:14])([F:13])[CH:10]([F:12])[F:11])[CH:7]=1.[F:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][C:33]=1[C:41]([F:44])([F:43])[F:42].CCN(CC)CC>C(Cl)Cl>[F:31][C:32]1[CH:40]=[CH:39][C:35]([C:36]([NH:23][C@@:15]([C:4]2[CH:5]=[C:6]([O:8][C:9]([F:14])([F:13])[CH:10]([F:12])[F:11])[CH:7]=[C:2]([F:1])[CH:3]=2)([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:37])=[CH:34][C:33]=1[C:41]([F:42])([F:43])[F:44]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 1442534-Fluoro-3-(trifluoromethyl)benzoyl ChlorideHCID 59458485(R)-1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-1-(4-fluorophenyl)-2-phenylethanamine

Produkt 1

HCID 23582278HCID 23582278, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (R)-1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-1-(4-fluorophenyl)-2-phenylethanamine (30 mg, 0.079 mmol) in CH2Cl2 (0.2 mL) was added 4-fluoro-3-(trifluoromethyl)benzoyl chloride (0.048 mL, 0.158 mmol), followed by Et3N (0.04 mL, 0.158 mmol). The resulting mixture was stirred at room temperature for 5 h. The crude product was purified on a preparative HPLC column type using 30 to 100% CH3CN in H2O with 0.1% TFA for 10 minutes as mobile phase. The solvent was removed under reduced pressure to afford (R)-4-fluoro-N-(1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-1-(4-fluorophenyl)-2-phenylethyl)-3-(trifluoromethyl)benzamide (35 mg, 80% yield) as white powder. LC-MS (ESI) 568.30 (M+H), retention time=4.27 min (0-100% MeOH in H2O with 0.1% TFA in a 4-min run); Analytical HPLC: 3.95 min (0-100% CH3CN in H2O with 0.1% TFA in a 4-min run, purity 100%); 1H NMR (400 MHz, CD3OD) δ ppm 3.88-4.01 (m, 1H), 4.10 (d, J=13.18 Hz, 1H), 6.69 (d, J=7.47 Hz, 2H), 6.97-7.51 (m, 11H), 7.99 (d, J=5.71 Hz, 2H), 8.90 (s, 1H).

Aufarbeitung

  1. customThe crude product was purified on a preparative HPLC column type
  2. customfor 10 minutes
  3. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3d6ac3bfa4484641999e6cb3208124de
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642576B2

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