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Dimethylformamide → HCID 67131174, Verbindung

HRID 1678639
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1678639
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]([CH:19]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[OH:20])=[C:17]3[C:12]([CH:13]=[CH:14][CH:15]=[CH:16]3)=[N:11]2)=[CH:6][CH:5]=1.COC(=O)[C:30]1[CH:35]=[CH:34][C:33](CCl)=[CH:32][CH:31]=1.C1C[O:42][CH2:41]C1.[CH3:44]S(C)=O.CN([CH:51]=[O:52])C>>[CH3:41][O:42][C:51](=[O:52])[C:24]1[CH:23]=[CH:22][C:21]([C:19]([C:18]2[N:10]([C:7]3[CH:8]=[CH:9][C:4]([Cl:3])=[CH:5][CH:6]=3)[N:11]=[C:12]3[C:17]=2[CH:16]=[CH:15][CH:14]=[CH:13]3)([CH:32]2[CH2:31][CH2:30][CH2:35][CH2:34][CH2:33]2)[O:20][CH3:44])=[CH:26][CH:25]=1
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Komponenten

6

Edukt 5

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 36664Methyl 4-(chloromethyl)benzoateHCID 21830753dimethylsulfoxide THFHCID 67130979[2-(4-Chloro-phenyl)-2H-indazol-3-yl]-cyclohexyl-methanol

Produkt 1

HCID 67131174HCID 67131174, Verbindung
Ausbeute 22 %

Versuchsvorschrift

Sodium hydride (14 mg, 293 umol) was added to an ice cold solution of [2-(4-chloro-phenyl)-2H-indazol-3-yl]-cyclohexyl-methanol (50 mg, 147 umol; example 10.1) in DMF (4.5 ml) under an argon atmosphere. After 30 min. methyl-4-(chloromethyl)benzoate (41 mg, 220 umol; CAS Reg. No. 34040-64-7) was added. The mixture was stirred at ambient temperature for 5 h, poured onto ice water/brine 1/1 and extracted two times with iPrOAc. The combined extracts were washed with ice water/brine 1/1 and dried over Na2SO4. After filtration the solvent was removed under reduced pressure to give the crude product as brown oil which was purified by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water to give the title compound (16 mg, 33 μmol; 22%) as yellow solid. MS: m/e=489.4 [M+H+].

Aufarbeitung

  1. addition34040-64-7) was added
  2. extractionextracted two times with iPrOAc
  3. washThe combined extracts were washed with ice water/brine 1/1
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration the solvent
  6. customwas removed under reduced pressure
  7. customto give the crude product as brown oil which
  8. customwas purified by preparative HPLC on reversed phase
  9. washeluting with a gradient of acetonitrile/water

Quellen und Nachweise

ORD-Eintrag
ord-8366ed01ed194d7aab678679114a9b28
Quelldatensatz
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08008505B2

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