Diisopropylethylamine → HCID 178463334, Verbindung

HRID 1943490

Reaktionsgleichung

Reaktionsgleichung von HRID 1943490
Cl[C:2]1[CH:3]=[C:4]([NH:21][CH2:22][CH3:23])[C:5]2[N:6]([C:8]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][N:17]=[CH:16][C:15]=3[F:20])=[O:12])=[CH:9][N:10]=2)[N:7]=1.[C@H:24]1([NH2:31])[CH2:29][CH2:28][C@H:27]([NH2:30])[CH2:26][CH2:25]1.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>CN1C(=O)CCC1.O>[NH2:30][C@H:27]1[CH2:28][CH2:29][C@H:24]([NH:31][C:2]2[CH:3]=[C:4]([NH:21][CH2:22][CH3:23])[C:5]3[N:6]([C:8]([C:11]([NH:13][C:14]4[CH:19]=[CH:18][N:17]=[CH:16][C:15]=4[F:20])=[O:12])=[CH:9][N:10]=3)[N:7]=2)[CH2:25][CH2:26]1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 596247296-chloro-8-(ethylamino)-N-(3-fluoropyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamideHCID 178511674HCID 178511674, Verbindung

Produkt 1

HCID 178463334HCID 178463334, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 82A (62.7 mg, 0.187 mmol), trans-cyclohexane-1,4-diamine (214 mg, 1.873 mmol) and DIEA (0.033 mL, 0.187 mmol) in NMP (1 mL) was heated in a microwave reactor at 120° C. for 50 minutes. The resulting mixture was diluted with water and made basic with saturated aqueous NaHCO3. The resulting solid was collected by filtration and dried under vacuum to give 6-((trans)-4-aminocyclohexylamino)-8-(ethylamino)-N-(3-fluoropyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamide as an off white solid (66.1 mg). HPLC Rt=2.122 minutes (Chromolith SpeedROD 4.6×50 mm, 10-90% aqueous methanol containing 0.1% TFA, 4 min gradient, monitored at 220 nm). [M+H]=413.

Aufarbeitung

  1. filtrationThe resulting solid was collected by filtration
  2. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-66ffb10074e540dda950a7d9e8774aec
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389527B2

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