Triethylamine → phenyl 1-(2-pyrrolidin-1-ylethyl)-1H-indazol-6-ylcarbamate

HRID 1790138Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1790138
[N:1]1([CH2:6][CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH2:17])[CH:15]=3)[CH:10]=[N:9]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:26]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:27]>C1COCC1>[N:1]1([CH2:6][CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:26](=[O:27])[O:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:15]=3)[CH:10]=[N:9]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 112762881-(2-Pyrrolidin-1-YL-ethyl)-1H-indazol-6-ylamine

Produkt 1

HCID 69652698phenyl 1-(2-pyrrolidin-1-ylethyl)-1H-indazol-6-ylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-6-ylamine (0.220 g, 0.955 mmol) and triethylamine (0.240 mL, 1.72 mmol) in 1 mL of THF at 0 C was slowly added phenyl chloroformate (0.246 ml, 1.72 mmol). The mixture was stirred cold for 1 hours and the formed precipitate collected by filtration with rinsing with ether to provide the title compound. 1H NMR (300 MHz, DMSO-D6) δ ppm 1.82 (m, 2 H), 1.97 (m, 2 H), 2.97 (m, 2 H), 3.49 (m, 2 H), 3.69 (m, 2 H), 4.71 (t, J=6.27 Hz, 2 H), 7.19 (m, 1 H), 7.28 (m, 3 H), 7.46 (m, 2 H), 7.74 (m, 1 H), 7.99 (m, 1 H), 8.10 (s, 1 H), 10.51 (s, 1 H); MS (DCI/NH3) m/z 351 [M+H]+.

Aufarbeitung

  1. filtrationthe formed precipitate collected by filtration
  2. washwith rinsing with ether

Quellen und Nachweise

ORD-Eintrag
ord-be0dfe59a2b64a20927446459a008702
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07071182B2

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