Triethylamine → (4-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)-3-methylbutanoyl)-4-methylpiperazine

HRID 1684015

Reaktionsgleichung

Reaktionsgleichung von HRID 1684015
[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][CH:19]([CH3:24])[CH2:20][C:21](O)=[O:22])=[C:8]2[CH3:25])=[CH:4][CH:3]=1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N.[CH3:45][N:46]1[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]1>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][CH:19]([CH3:24])[CH2:20][C:21]([N:49]3[CH2:50][CH2:51][N:46]([CH3:45])[CH2:47][CH2:48]3)=[O:22])=[C:8]2[CH3:25])=[CH:26][CH:27]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 76257Diethyl cyanophosphonateHCID 98673334-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)-3-methylbutanoic acid

Produkt 1

HCID 19041728(4-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)-3-methylbutanoyl)-4-methylpiperazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of the acid from Example 7, Step 6 (300 mg) in DMF (4 mL) was added triethylamine (0.13 mL), diethyl cyanophosphonate (0.13 mL) and 1-methylpiperazine (0.08 mL) at r.t. After 4 h the reaction mixture was diluted with EtOAc and the organic phase was washed with HCl 1M, 5% aqueous NaHCO3 and brine, dried (MgSO4) and evaporated. Flash chromatography of the residue (silica gel; CH2Cl2 /MeOH, 95:5) afforded the title compound as a white solid.

Aufarbeitung

  1. washthe organic phase was washed with HCl 1M, 5% aqueous NaHCO3 and brine
  2. dry with materialdried (MgSO4)
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-1b334975065b430cb5d670230529c4ef
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05639780

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