StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Triethylamine → Methyl 3-[4-({3-[bis(4-methoxyphenyl)phenylmethoxy]propyl}-{4-[(2-chloro-4-nitrophenyl)diazenyl]phenyl}amino)butanoyl]pyrrolo[4,5-e]indoline-7-carboxylate

HRID 481178
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 481178
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:56]2[CH:61]=[CH:60][C:59]([O:62][CH3:63])=[CH:58][CH:57]=2)([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[O:10][CH2:11][CH2:12][CH2:13][N:14]([C:32]2[CH:37]=[CH:36][C:35]([N:38]=[N:39][C:40]3[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][C:41]=3[Cl:49])=[CH:34][CH:33]=2)[CH2:15][CH2:16][CH2:17][C:18](OC2C(F)=C(F)C(F)=C(F)C=2F)=[O:19])=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH:71]1[C:75]2=[C:76]3[C:80](=[CH:81][CH:82]=[C:74]2[NH:73][CH:72]=1)[NH:79][CH:78]([C:83]([O:85][CH3:86])=[O:84])[CH2:77]3>CN(C=O)C>[CH3:63][O:62][C:59]1[CH:60]=[CH:61][C:56]([C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[O:10][CH2:11][CH2:12][CH2:13][N:14]([C:32]2[CH:37]=[CH:36][C:35]([N:38]=[N:39][C:40]3[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][C:41]=3[Cl:49])=[CH:34][CH:33]=2)[CH2:15][CH2:16][CH2:17][C:18]([N:73]2[C:74]3[C:75](=[C:76]4[C:80](=[CH:81][CH:82]=3)[NH:79][CH:78]([C:83]([O:85][CH3:86])=[O:84])[CH2:77]4)[CH:71]=[CH:72]2)=[O:19])=[CH:57][CH:58]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 66717311Methyl pyrrolo[4,5-e]indoline-7-carboxylateHCID 865847202,3,4,5,6-Pentafluorophenyl 4-({3-[bis(4-methoxyphenyl)phenylmethoxy]propyl}{4-[(2-chloro-4-nitrophenyl)diazenyl]phenyl}amino)butanoate

Produkt 1

HCID 86587108Methyl 3-[4-({3-[bis(4-methoxyphenyl)phenylmethoxy]propyl}-{4-[(2-chloro-4-nitrophenyl)diazenyl]phenyl}amino)butanoyl]pyrrolo[4,5-e]indoline-7-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 22 (3.0 g, 3.37 mmol) in 15 mL anhydrous DMF is added triethylamine (0.75 mL) followed by methyl pyrrolo[4,5-e]indoline-7-carboxylate (Boger, et al., J. Org. Chem. 52:1521 (1987)) (0.8 g, 3.7 mmol). The resultant solution is stored at room temperature for 20 h. The reaction is analyzed by HPLC to confirm its completeness. DMF is removed on a rotary evaporator equipped with an oil pump. The residue, dark syrup is suspended in 50% ethylacetate/hexanes (˜25 mL). The mixture is sonicated to initiate the crystallization. The crystals are stirred for 15 min, collected by filtration on a sintered glass funnel, washed with methanol (2×30 mL) and dried under vacuum. The yield of the desired product is 2.7 g (87%) as a deep-purple solid. 1H NMR (DMSO-d6) δ11.93 (d, J=1.7 Hz, indole NH, 1H), 8.43 (d, J=2.5 Hz, aromatic proton, 1H), 8.3-8.2 (m, aromatic protons, 2H), 7.85-7.75 (m, aromatic protons, 3H), 7.45-7.18 (m, aromatic protons, 10H), 7.05 (d, J=1.8 Hz, aromatic proton, 1H), 6.97 (d, J=9 Hz, aromatic protons, 2H), 6.87 (d, J=9 Hz, aromatic protons, 4H), 4.12 (t, J=8 Hz, aliphatic protons, 2H), 3.87 (s, ester CH3, 3H), 3.71 (s, CH3, 6H), 3.60 (br t, aliphatic protons, 2H), 3.45 (br t, aliphatic protons, 2H), 3.29 (br t, aliphatic protons, 2H), 3.08 (t, J=5 Hz, aliphatic protons, 2H), 2.5 (br t, obscured by DMSO signal, aliphatic protons, 2H), 1.88 (br m, aliphatic protons, 4H).

Aufarbeitung

  1. customDMF is removed on a rotary evaporator
  2. customequipped with an oil pump
  3. customThe mixture is sonicated
  4. customthe crystallization
  5. filtrationcollected by filtration on a sintered glass funnel
  6. washwashed with methanol (2×30 mL)
  7. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-10876c480fda4b28935c09f951d2e173
Quelldatensatz
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06653473B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion