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Methanol → 4-(2-{4-[2-Fluoro-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)-2-(methyloxy)benzonitrile

HRID 1187123
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Reaktionsgleichung

Reaktionsgleichung von HRID 1187123
Cl.[F:2][CH:3]([C:11]1[CH:20]=[CH:19][C:14]2[C:15](=[O:18])[O:16][CH2:17][C:13]=2[C:12]=1[CH3:21])[CH2:4][N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.[CH3:22][O:23][C:24]1[CH:31]=[C:30]([CH2:32][CH:33]=O)[CH:29]=[CH:28][C:25]=1[C:26]#[N:27].C([BH3-])#N.[Na+].CO>CC(O)=O>[F:2][CH:3]([C:11]1[CH:20]=[CH:19][C:14]2[C:15](=[O:18])[O:16][CH2:17][C:13]=2[C:12]=1[CH3:21])[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH2:33][CH2:32][C:30]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24]([O:23][CH3:22])[CH:31]=2)[CH2:7][CH2:6]1
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Komponenten

6

Edukt 4

HCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 666467295-(1-fluoro-2-piperazin-1-ylethyl)-4-methyl-2-benzofuran-1(3H)-one hydrochlorideHCID 772312592-(Methyloxy)-4-(2-oxoethyl)benzonitrile

Produkt 1

HCID 498010424-(2-{4-[2-Fluoro-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)-2-(methyloxy)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

5-(1-Fluoro-2-piperazin-1-ylethyl)-4-methyl-2-benzofuran-1(3H)-one hydrochloride (30 mg, 0.11 mmol), 2-(methyloxy)-4-(2-oxoethyl)benzonitrile (37 mg, 0.22 mmol), sodium cyanoborohydride (67 mg, 1.078 mmol) were added to a 25 mL flask containing a stir bar; to the flask was added MeOH (3 mL) and few drops of AcOH. The reaction mixture was subsequently stirred for 12 h r; LC indicated that reaction had gone to completion. The solution was concentrated to dryness, redissolved in EtOAc (15 mL) and washed with aq. NaHCO3 and aq. NaCl. The organic phase was dried over Na2SO4, filtered and concentrated to dryness. It was then re-dissolved in MeOH (3.5 mL) again, filtered and shot into mass-directed HPLC for separation to give the desired product. LC-MS (IE, m/z): 450 [M+1]+.

Aufarbeitung

  1. additioncontaining a stir bar
  2. customLC indicated that reaction
  3. concentrationThe solution was concentrated to dryness
  4. dissolutionredissolved in EtOAc (15 mL)
  5. washwashed with aq. NaHCO3 and aq. NaCl
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. dissolutionIt was then re-dissolved in MeOH (3.5 mL) again
  10. filtrationfiltered
  11. customshot into mass-directed HPLC for separation

Quellen und Nachweise

ORD-Eintrag
ord-184e67def2b942d9b8c8a5876c2fe5ef
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08673920B2

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