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Diisopropylethylamine → 3,5-dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-ethylbenzamide

HRID 875460
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 875460
[Cl:1][C:2]1[CH:10]=[C:9]([C:11](=[O:15])[NH:12][CH2:13][CH3:14])[CH:8]=[C:7]([Cl:16])[C:3]=1[C:4]([OH:6])=O.ON1C2N=CC=CC=2N=N1.C[NH3+].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.[NH:60]1[C:68]2[CH:67]=[CH:66][N:65]=[C:64]([NH:69][C:70]([CH:72]3[CH2:74][CH2:73]3)=[O:71])[C:63]=2[CH:62]=[CH:61]1.C(N(CC)C(C)C)(C)C>CN(C)C1C=CC=CC=1.O>[Cl:16][C:7]1[CH:8]=[C:9]([CH:10]=[C:2]([Cl:1])[C:3]=1[C:4]([N:60]1[C:68]2[CH:67]=[CH:66][N:65]=[C:64]([NH:69][C:70]([CH:72]3[CH2:73][CH2:74]3)=[O:71])[C:63]=2[CH:62]=[CH:61]1)=[O:6])[C:11]([NH:12][CH2:13][CH3:14])=[O:15]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 710615382,6-Dichloro-4-(ethylcarbamoyl)benzoic acidHCID 866211442-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate MethanaminiumHCID 86720627N-(1H-pyrrolo[3,2-c]pyridin-4-yl)cyclopropanecarboxamide

Produkt 1

HCID 71618615
3,5-dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-ethylbenzamide
Ausbeute 26,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 949N,N-DimethylanilineLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A well stirred mixture of 2,6-dichloro-4-(ethylcarbamoyl)benzoic acid (84.6 mg, 0.42 mmol), 1-hydroxy-7-azabenzotriazole (77 mg, 0.57 mmol), N,N-dimethyl aminopyridine (22 mg, 0.11 mmol) and 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate methanaminium (216 mg, 0.57 mmol) in N,N-dimethylaniline was treated with N-(1H-pyrrolo[3,2-c]pyridin-4-yl)cyclopropanecarboxamide (100 mg, 0.38 mmol) and N,N-diisopropylethylamine (0.1 ml, 0.95 mmol). The reaction was stirred overnight at room temperature. The contents were diluted with water and extracted with ethyl acetate. The combined organic portion was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography using methanol in dichloromethane (3%) as eluent to yield 3,5-dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-ethylbenzamide (45 mg, 26%) as an off white solid.

Aufarbeitung

  1. stirringThe reaction was stirred overnight at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe combined organic portion was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c703f7b398524637bd99cf1fe0b0f3a0
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08980911B2

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