1,2-Dichloroethane → N-[(1S,2S)-2-{[3-Methyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxamide

HRID 1750643

Reaktionsgleichung

Reaktionsgleichung von HRID 1750643
Cl.C[N:3]([C:10]1[CH:15]=[N:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]=1)[C@H:4]1[CH2:8][CH2:7][CH2:6][C@@H:5]1[NH2:9].[N:20]1[N:21]([C:25]2[C:26]([C:31]([OH:33])=O)=[N:27][CH:28]=[CH:29][CH:30]=2)[N:22]=[CH:23][CH:24]=1.[CH2:34](Cl)CCl.N1C2C(=NC=CC=2)N(O)N=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:34][C:15]1[C:10]([NH:3][C@H:4]2[CH2:8][CH2:7][CH2:6][C@@H:5]2[NH:9][C:31]([C:26]2[C:25]([N:21]3[N:22]=[CH:23][CH:24]=[N:20]3)=[CH:30][CH:29]=[CH:28][N:27]=2)=[O:33])=[N:11][CH:12]=[C:13]([C:16]([F:17])([F:18])[F:19])[N:14]=1

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 181649HOAtHCID 667422883-[1,2,3]Triazol-2-yl-pyridine-2-carboxylic acidHCID 118308127(1S,2S)-1-N-Methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride2×

Produkt 1

HCID 118308165N-[(1S,2S)-2-{[3-Methyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of (1S,2S)-1-N-methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 23; 60 mg, 0.20 mmol), 3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxylic acid (CAS number 1252907-86-0; 40 mg, 0.21 mmol), EDC (58 mg, 0.30 mmol), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (41 mg, 0.30 mmol) and triethylamine (0.085 ml, 0.61 mmol) in DCM (1 ml) was stirred at room temperature over the weekend. The reaction was concentrated in vacuo and was then purified by column chromatography (basic silica, 20 to 100% ethyl acetate/petrol) followed by column chromatography (silica, 0 to 100% ethyl acetate/petrol) to afford the title compound.

Aufarbeitung

  1. concentrationThe reaction was concentrated in vacuo
  2. customwas then purified by column chromatography (basic silica, 20 to 100% ethyl acetate/petrol)

Quellen und Nachweise

ORD-Eintrag
ord-96d3eb83dd814945b9279c16465daaa3
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156829B2

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