HCID 59624544, Verbindung → HCID 178511619, Verbindung

HRID 1943423Notizen

Reaktionsgleichung

[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:10]3[N:11]([C:16]([C:19]([NH:21][C:22]4[CH:27]=[CH:26][N:25]=[CH:24][C:23]=4[F:28])=[O:20])=[CH:17][N:18]=3)[N:12]=[C:13](Cl)[CH:14]=2)[CH:5]=[CH:4][CH:3]=1.[C@H:29]1([NH2:36])[CH2:34][CH2:33][C@H:32]([NH2:35])[CH2:31][CH2:30]1>CN1C(=O)CCC1>[NH2:35][C@H:32]1[CH2:33][CH2:34][C@H:29]([NH:36][C:13]2[CH:14]=[C:9]([NH:8][C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=3)[C:10]3[N:11]([C:16]([C:19]([NH:21][C:22]4[CH:27]=[CH:26][N:25]=[CH:24][C:23]=4[F:28])=[O:20])=[CH:17][N:18]=3)[N:12]=2)[CH2:30][CH2:31]1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A mixture of 8-(6-bromopyridin-2-ylamino)-6-chloro-N-(3-fluoropyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamide 17A (550 mg, 1.189 mmol) and trans-cyclohexane-1,4-diamine (1.086 g, 9.51 mmol) in NMP (4 mL) was heated at 100° C. overnight. The reaction mixture was cooled to room temperature, and then added to ice water. The yellow solid was collected by filtration, and rinsed with water. The still wet solid pad was azeotroped with DCM/MeOH three times. The resulting solid residue was treated with a small amount of MeOH, filtered and dried to give 17B (456 mg, 71%) as a yellow solid. MS (m+1)=540. HPLC Peak Rt=2.870 minutes. (Chromolith column 4.6×50 mm eluting with 10-90% aqueous methanol over 4 minutes containing 0.1% TFA, 4 mL/min, monitoring at 220 nm).

Aufarbeitung

temperatureThe reaction mixture was cooled to room temperature
filtrationThe yellow solid was collected by filtration
washrinsed with water
customThe still wet solid pad was azeotroped with DCM/MeOH three times
additionThe resulting solid residue was treated with a small amount of MeOH
filtrationfiltered
customdried

Quellen und Nachweise

ORD-Eintrag: ord-d79aab27551f44fdbbb97c04aace2555
Quelldatensatz: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08389527B2

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