Sodium Bicarbonate → methyl 1-hydroxymethyl-5-nitro-3-[(5,6,7-trimethoxyindol-2-yl)carbonyl]-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylate

HRID 366837

Reaktionsgleichung

Reaktionsgleichung von HRID 366837
C([O:5][C:6]([N:8]1[C:19]2[C:11](=[C:12]3[C:16](=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=2)[NH:15][C:14]([C:23]([O:25][CH3:26])=[O:24])=[CH:13]3)[CH:10]([CH2:27][OH:28])[CH2:9]1)=O)(C)(C)C.CCN=C=NCCCN(C)C.Cl.[CH3:41][O:42][C:43]1[CH:44]=[C:45]2[C:49](=[C:50]([O:54][CH3:55])[C:51]=1[O:52][CH3:53])[NH:48][C:47](C(O)=O)=[CH:46]2.C([O-])(O)=O.[Na+]>Cl.CC(N(C)C)=O>[OH:28][CH2:27][CH:10]1[C:11]2=[C:12]3[C:16](=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[C:19]2[N:8]([C:6]([C:47]2[NH:48][C:49]4[C:45]([CH:46]=2)=[CH:44][C:43]([O:42][CH3:41])=[C:51]([O:52][CH3:53])[C:50]=4[O:54][CH3:55])=[O:5])[CH2:9]1)[NH:15][C:14]([C:23]([O:25][CH3:26])=[O:24])=[CH:13]3

Komponenten

7

Edukt 4

HCID 516892Sodium BicarbonateHCID 8210525,6,7-Trimethoxy-1H-indole-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10739197methyl 3-(t-butyloxycarbonyl)-1-hydroxymethyl-5-nitro-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylate

Produkt 1

HCID 10577983methyl 1-hydroxymethyl-5-nitro-3-[(5,6,7-trimethoxyindol-2-yl)carbonyl]-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylateAusbeute 71,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A solution of 29 (1.52 g, 3.87 mmol) in HCl-saturated dioxane (120 mL) was stirred for 100 min (until TLC indicated complete reaction) and the suspension was evaporated. EDCI.HCl (1.48 g, 7.74 mmol) and 5,6,7-trimethoxyindole-2-carboxylic acid (0.97 g, 3.87 mmol) in DMA (12 mL) were added, and the mixture stirred at 20° C. for 16 h. Dilute aq NaHCO3 (100 mL) was added, and the precipitated solid was filtered off, washed with H2O, and dried. Trituration with hot MeOH gave methyl 1-hydroxymethyl-5-nitro-3-[(5,6,7-trimethoxyindol-2-yl)carbonyl]-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylate (56) as an orange powder (1.45 g, 71%), mp 239-240.5° C. (dec.). 1H NMR [(CD3)2SO] δ 11.46 (d, J=32 1.6 Hz, 1 H, NH), 11.30 (s, 1 H, NH), 9.19 (s, 1 H, H-4), 7.54 (s, 1 H, H-8), 7.09 (s, 1 H, H-3'), 6.95 (s, 1 H, H-4'), 5.11 (t, J=5.3 Hz, 1 H, OH), 4.71 (t, J=10.1 Hz, 1 H, H-2), 4.47 (dd, J=10.6, 4.1 Hz, 1 H, H-2), 4.02-3.95 (m, 1 H), 3.94 (s, 3 H, OMe), 3.93 (s, 3 H, OMe), 3.82 (s, 3 H, OMe), 3.80 (s, 3 H, OMe), 3.81-3.75 (m, 2 H). Anal. Calculated for C25H24N4O9.1/2H2O: C, 56.3; H, 4.7; N, 10.5. Found: C, 56.4; H, 4.4; N, 10.3%.

Aufarbeitung

  1. custom(until TLC indicated complete reaction)
  2. customthe suspension was evaporated
  3. filtrationthe precipitated solid was filtered off
  4. washwashed with H2O
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-637073e0609c4108b435cc75bdf8234e
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06130237

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