Trifluoroacetic acid → HCID 57418643, Verbindung

HRID 2354382Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2354382
[C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][C:4]([CH:7]([NH:14][CH3:15])[CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:3][CH:2]=1.[CH2:22]([O:24][C:25]([C:27]1[CH:28]=[CH:29][C:30]2[O:35][CH2:34][C:33](=[O:36])[N:32]([CH2:37][C:38]([OH:40])=O)[C:31]=2[CH:41]=1)=[O:26])[CH3:23].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.FC(F)(F)C(O)=O>C(Cl)Cl.CC#N.O>[C:1]1([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:6]=[CH:5][C:4]([CH:7]([N:14]([CH3:15])[C:38](=[O:40])[CH2:37][N:32]2[C:31]3[CH:41]=[C:27]([C:25]([O:24][CH2:22][CH3:23])=[O:26])[CH:28]=[CH:29][C:30]=3[O:35][CH2:34][C:33]2=[O:36])[CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:3][CH:2]=1

Komponenten

8

Edukt 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27567161-([1,1'-Biphenyl]-4-yl)-N-methyl-2-(pyrrolidin-1-yl)ethan-1-amineHCID 57457165HCID 57457165, Verbindung

Produkt 1

HCID 57418643HCID 57418643, VerbindungAusbeute 77,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 18373917Acetonitrile--water (1/1)Lösungsmittel

Versuchsvorschrift

[1-(4-biphenylyl)-2-(1-pyrrolidinyl)ethyl]methylamine (0.5 g, 1.8 mmol) and {6-[(ethyloxy)carbonyl]-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl}acetic acid (0.63 g, 2.0 mmol) were dissolved in 10 mL of methylene chloride. Triethylamine (1.0 mL, 7.1 mmol) was delivered to the room temperature mixture, and the solution was allowed to stir for several minutes before a separate solution of 1H-1,2,3-benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium hexafluorophosphate (BOP reagent, 0.89 g, 2.0 mmol) dissolved in 4 mL of methylene chloride was added at room temperature to the mixture. The reaction was maintained at that temperature for 72 hours, before it was determined to be complete by LCMS (two Aquasil C18, 20×1 mm columns were run in sequence, 4 minutes at 0.1 mL/min, 1-99% CH3CN/H2O with 0.018% trifluoroacetic acid, ES) Rt=2.7 min and m/e 542 [M+1]+. Solvent was removed by rotary evaporation and the crude residue was purified by prep HPLC (Waters, 50×100 mm, 84 mL/min, A: acetonitrile B: water (pH=10, NH4OH), A: 10 to 99% over 15 min, UV detection at 214 nm) to give the title compound (0.75 g. 1.4 mmol, 77%) as a pale yellow amorphous solid. MS (ES) m/e 542 [M+H]+.

Aufarbeitung

  1. customwas delivered to the room temperature mixture
  2. additionwas added at room temperature to the mixture
  3. temperatureThe reaction was maintained at that temperature for 72 hours, before it
  4. customSolvent was removed by rotary evaporation
  5. customthe crude residue was purified by prep HPLC (Waters, 50×100 mm, 84 mL/min

Quellen und Nachweise

ORD-Eintrag
ord-cde170a8834345c39579701bb1cecb90
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07749998B2

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