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Ethylenediamine → 2-(1-benzyl-6-chloro-1H-indazol-3-yl)-N-isopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 246448
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 246448
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[C:10]([C:18]2[N:19]=[C:20]3[C:26]([C:27]([NH:29][CH:30]([CH3:32])[CH3:31])=[O:28])=[CH:25][N:24](COCC[Si](C)(C)C)[C:21]3=[N:22][CH:23]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C(N)CN>ClCCl>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[C:10]([C:18]2[N:19]=[C:20]3[C:26]([C:27]([NH:29][CH:30]([CH3:32])[CH3:31])=[O:28])=[CH:25][NH:24][C:21]3=[N:22][CH:23]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 712800812-(1-benzyl-6-chloro-1H-indazol-3-yl)-N-isopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Produkt 1

HCID 712799822-(1-benzyl-6-chloro-1H-indazol-3-yl)-N-isopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamideAusbeute 115,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

2-(1-Benzyl-6-chloro-1H-indazol-3-yl)-N-isopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (87 mg, 151 μmol) was dissolved in dichloromethane (25 mL) and to this was added trifluoroacetic acid (1.72 g, 1.17 mL, 15.1 mmol). The mixture was stirred for 4 h then concentrated in vacuo. The residue was diluted in dichloromethane and re-concentrated again, then suspended in dichloromethane and ethylenediamine (682 mg, 0.766 mL, 11.3 mmol) added. The mixture was stirred for 15 h then concentrated in vacuo. The residue was triturated with water and the solid collected by filtration and dried. The solid was adsorbed onto silica gel and purified by chromatography (silica, SiliCycle 25 g cartridge, 0-5% methanol in dichloromethane, 15 min gradient) to give 2-(1-benzyl-6-chloro-1H-indazol-3-yl)-N-isopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (78 mg, 175 μmol, quantitative) as a pale yellow powder. MS (M−H)−=443; 1H NMR (DMSO-d6) δ: 12.84 (br. s., 1H), 9.05-9.13 (m, 1H), 8.37-8.50 (m, 2H), 8.08 (d, J=1.1 Hz, 1H), 8.01 (d, J=7.6 Hz, 1H), 7.23-7.38 (m, 6H), 5.79 (s, 2H), 4.20 (dq, J=13.6, 6.7 Hz, 1H), 1.30 (d, J=6.4 Hz, 6H).

Aufarbeitung

  1. concentrationthen concentrated in vacuo
  2. additionThe residue was diluted in dichloromethane
  3. concentrationre-concentrated again
  4. stirringThe mixture was stirred for 15 h
  5. concentrationthen concentrated in vacuo
  6. customThe residue was triturated with water
  7. filtrationthe solid collected by filtration
  8. customdried
  9. custompurified by chromatography (silica, SiliCycle 25 g cartridge, 0-5% methanol in dichloromethane, 15 min gradient)

Quellen und Nachweise

ORD-Eintrag
ord-50cc1e2234064989b2d820ca0c57da58
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08658646B2

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