Diisopropylethylamine → (S)-1-(4-Chloro-6-(3-cyclopropyl-1H-pyrazol-5-ylamino)-1,3,5-triazin-2-yl)-2-methyl-N-(pyrazin-2-yl)pyrrolidine-2-carboxamide

HRID 1961380Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1961380
C([N:4](C(C)C)CC)(C)C.Cl[C:11]1[N:16]=[C:15]([Cl:17])[N:14]=[C:13]([NH:18][C:19]2[NH:23][N:22]=[C:21]([CH:24]3[CH2:26][CH2:25]3)[CH:20]=2)[N:12]=1.F[C:28]1[N:33]=[CH:32][C:31]([NH:34][C:35]([C@:37]2([CH3:42])[CH2:41][CH2:40][CH2:39][NH:38]2)=[O:36])=C[CH:29]=1>C1COCC1>[Cl:17][C:15]1[N:14]=[C:13]([NH:18][C:19]2[NH:23][N:22]=[C:21]([CH:24]3[CH2:26][CH2:25]3)[CH:20]=2)[N:12]=[C:11]([N:38]2[CH2:39][CH2:40][CH2:41][C@@:37]2([CH3:42])[C:35]([NH:34][C:31]2[CH:32]=[N:33][CH:28]=[CH:29][N:4]=2)=[O:36])[N:16]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 59436446(S)-N-(6-Fluoropyridin-3-yl)-2-methylpyrrolidine-2-carboxamideHCID 178478357HCID 178478357, Verbindung

Produkt 1

HCID 178431749(S)-1-(4-Chloro-6-(3-cyclopropyl-1H-pyrazol-5-ylamino)-1,3,5-triazin-2-yl)-2-methyl-N-(pyrazin-2-yl)pyrrolidine-2-carboxamideAusbeute 69,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Diisopropylethylamine (0.77 mL, 4.42 mmol) was added to a mixture of 4,6-dichloro-N-(3-cyclopropyl-1H-pyrazol-5-yl)-1,3,5-triazin-2-amine (800 mg, 2.95 mmol) and (S)—N-(6-fluoropyridin-3-yl)-2-methylpyrrolidine-2-carboxamide (625 mg, 2.8 mmol) in THF (20 mL). The reaction mixture was stirred at room temperature overnight and the product was separated by preparative HPLC. Removal of the solvents furnished 8B (860 mg, 64%) as a TFA salt. LC/MS [M+H]+: 440; Ret time (Method C): 2.33 min.

Aufarbeitung

  1. customthe product was separated by preparative HPLC
  2. customRemoval of the solvents

Quellen und Nachweise

ORD-Eintrag
ord-f51173a9fffc482eb94460975561134f
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415340B2

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