Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 57381862, Verbindung

HRID 1892555Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1892555
[F:1][C:2]1[C:7]2[C:8]([C:18](=[O:21])[NH:19][CH3:20])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[CH3:31])[C:25]([OH:27])=O.[N:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[C:38]1([NH2:42])[CH2:41][O:40][CH2:39]1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[F:1][C:2]1[C:7]2[C:8]([C:18]([NH:19][CH3:20])=[O:21])=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[C:22]1[CH:23]=[C:24]([C:25](=[O:27])[NH:42][C:38]2([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][N:32]=3)[CH2:39][O:40][CH2:41]2)[CH:28]=[CH:29][C:30]=1[CH3:31]

Komponenten

6

Edukt 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 592756803-(4-Fluoro-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)-4-methylbenzoic acidHCID 679576533-Pyridin-2-yloxetan-3-amine

Produkt 1

HCID 57381862HCID 57381862, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 3-(4-fluoro-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)-4-methylbenzoic acid (0.045 g, 0.107 mmol, 1.0 eq) and 3-(pyridin-2-yl)oxetan-3-amine.2HCl (0.025 g, 0.112 mmol, 1.05 eq) in DMF at 0° C. was added TEA (0.15 ml, 1.08 mmol, 10 eq) and BOP reagent (0.06 g, 0.136 mmol, 1.3 eq). The reaction mixture was stirred as rt overnight. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered and the filtrate concentrated. The crude product was purified by preparative HPLC. Yield: 0.015 g (25.4%).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated
  6. customThe crude product was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-0ab1d0c6f3e1405aad0aa31162cb878b
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507683B2

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