Water → 4-[1-Amino-4-[2-(3-hydroxy-phenyl)-ethylamino]-1-(3-methyl-3H-imidazol-4-yl)-butyl]-2-fluoro-benzonitrile

HRID 413433Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 413433
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:30]S(C(C)(C)C)=O)([C:24]2[N:25]([CH3:29])[CH:26]=[N:27][CH:28]=2)[CH2:10][CH2:11][CH2:12][NH:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22]C)[CH:17]=2)=[CH:5][C:4]=1[F:37])#[N:2].B(Br)(Br)Br.O>C(Cl)Cl>[NH2:30][C:9]([C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([F:37])[CH:5]=1)([C:24]1[N:25]([CH3:29])[CH:26]=[N:27][CH:28]=1)[CH2:10][CH2:11][CH2:12][NH:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 25134Boron tribromideHCID 865855192-Methyl-propane-2-sulfinic acid [1-(4-cyano-3-fluoro-phenyl)-4-[2-(3-methoxy-phenyl)-ethylamino]-1-(3-methyl-3-H-imidazol-4-yl)-butyl]-amide

Produkt 1

HCID 185332004-[1-Amino-4-[2-(3-hydroxy-phenyl)-ethylamino]-1-(3-methyl-3H-imidazol-4-yl)-butyl]-2-fluoro-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

2-Methyl-propane-2-sulfinic acid [1-(4-cyano-3-fluoro-phenyl)-4-[2-(3-methoxy-phenyl)-ethylamino]-1-(3-methyl-3-H-imidazol-4-yl)-butyl]-amide (0.075 g, 0.1427 mmol) was dissolved in CH2Cl2 (7 mL) with cooling in an ice-H2O bath, then treated with BBr3 (1 mL of a 1M solution in CH2Cl2, 1 mmol). After 15 min., H2O (3 mL) was added and the reaction mixture was concentrated in vacuo. The residue was dissolved in MeOH and stirred at ambient temperature for 15 min. Concentration to dryness gave the title compound which was used without further purification. MS (M+1) 408.

Aufarbeitung

  1. temperaturewith cooling in an ice-H2O bath
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in MeOH
  4. concentrationConcentration to dryness

Quellen und Nachweise

ORD-Eintrag
ord-e2001d3c7d0c44c8893b3f00f01c88e6
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06566385B2

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