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

HRID 1187125
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Reaktionsgleichung

Reaktionsgleichung von HRID 1187125
Cl.[CH2:2]([O:4][CH:5]([C:13]1[CH:22]=[CH:21][C:16]2[C:17](=[O:20])[O:18][CH2:19][C:15]=2[C:14]=1[CH3:23])[CH2:6][N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)[CH3:3].[CH3:24][O:25][C:26]1[CH:33]=[C:32]([CH2:34][CH:35]=O)[CH:31]=[CH:30][C:27]=1[C:28]#[N:29].C([BH3-])#N.[Na+].CC(O)=O>CO.CCOC(C)=O>[CH2:2]([O:4][CH:5]([C:13]1[CH:22]=[CH:21][C:16]2[C:17](=[O:20])[O:18][CH2:19][C:15]=2[C:14]=1[CH3:23])[CH2:6][N:7]1[CH2:12][CH2:11][N:10]([CH2:35][CH2:34][C:32]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[C:26]([O:25][CH3:24])[CH:33]=2)[CH2:9][CH2:8]1)[CH3:3]
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Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 675175415-[1-(ethyloxy)-2-piperazin-1-ylethyl]-4-methyl-2-benzofuran-1(3H)-one hydrochlorideHCID 772312592-(Methyloxy)-4-(2-oxoethyl)benzonitrile

Produkt 1

HCID 498010444-(2-{4-[2-(Ethyloxy)-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)-2-(methyloxy)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5-[1-(Ethyloxy)-2-piperazin-1-ylethyl]-4-methyl-2-benzofuran-1(3H)-one hydrochloride (50 mg, 0.16 mmol), 2-(methyloxy)-4-(2-oxoethyl)benzonitrile (40 mg, 0.23 mmol), sodium cyanoborohydride (14 mg, 1.7 mmol) and a stir bar were added to a 25 mL flask and few drops of AcOH. The resulting mixture was then dissolved in MeOH (3 mL) and stirred for 12 h; Analysis by LC indicated that reaction had gone to completion. The reaction mixture was treated with EtOAc (20 mL) and washed with aq. NaHCO3 and aq. NaCl. The organic phase was then dried over Na2SO4, filtered and concentrated to dryness; the resulting residue was then dissolved in MeOH (3.5 mL), filtered and shot into Mass-directed HPLC for separation to give the desired product. LC-MS (IE, m/z): 464 [M+1]+.

Aufarbeitung

  1. customAnalysis by LC indicated that reaction
  2. washwashed with aq. NaHCO3 and aq. NaCl
  3. dry with materialThe organic phase was then dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. dissolutionthe resulting residue was then dissolved in MeOH (3.5 mL)
  7. filtrationfiltered
  8. customshot into Mass-directed HPLC for separation

Quellen und Nachweise

ORD-Eintrag
ord-217a7a66d1d3401cb3c1c0f56c6dd879
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08673920B2

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