1H-Indole-5-Carboxylic Acid → 1h-Indole-5-carboxamide,n-(cyclopentylmethyl)-

HRID 728674

Reaktionsgleichung

Reaktionsgleichung von HRID 728674
[CH:1]1([CH2:6][NH2:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2)(O)=[O:9].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[CH:1]1([CH2:6][NH:7][C:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[CH:14]3)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

6

Edukt 3

HCID 742801H-Indole-5-Carboxylic AcidHCID 80153CyclopentanemethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 100373961h-Indole-5-carboxamide,n-(cyclopentylmethyl)-Ausbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of cyclopentylmethylamine (2.66 g), 5-carboxyindole (4.76 g), 4-(dimethylamino)pyridine (3.60 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (5.67 g) in dichloromethane (60 ml) was stirred for 12 hours under an atmosphere of nitrogen. The amber solution was diluted with dichloromethane (150 ml), washed successively with 10% (w/v) aqueous sodium carbonate, 10% (v/v) hydrochloric acid, water, and brine, dried (MgSO4), and evaporated. The residual amber oil was purified by flash chromatography on silica gel (700 ml), eluting with 1:3 v/v ethyl acetate:chloroform, to yield 5-(N-cyclopentylmethylcarbamoyl)indole (A) (5.17 g, 80%) as a white crystalline solid; mp 110°-112° C.; NMR (80 MHz, CDCl3): 1.0-2.4(broad m, 9H, cyclopentyl), 3.4(dd, 2H, CH2N), 6 2(broad, 1H, NH), 6.6(m, 1H, H3 -indole), 7.3(t, 1H, H2 -indole), 7.4(d, 1H, H7 -indole), 8.5(broad, 1H, CONH).

Aufarbeitung

  1. washwashed successively with 10% (w/v) aqueous sodium carbonate, 10% (v/v) hydrochloric acid, water, and brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residual amber oil was purified by flash chromatography on silica gel (700 ml)
  5. washeluting with 1:3 v/v ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-50ae42b281054f9cbd78bcf93d053f75
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05049679

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