Ethylamine → N-(4-{1,3-dimethyl-1H-pyrazolo[4,3-d]pyrimidin-7-yl}-6-[2-(1-methylisoquinolin-6-yl)ethynyl]pyridin-2-yl)-2-(ethylamino)butanamide

HRID 923673

Reaktionsgleichung

Reaktionsgleichung von HRID 923673
[CH3:1][N:2]1[C:10]2[C:9]([C:11]3[CH:16]=[C:15]([C:17]#[C:18][C:19]4[CH:20]=[C:21]5[C:26](=[CH:27][CH:28]=4)[C:25]([CH3:29])=[N:24][CH:23]=[CH:22]5)[N:14]=[C:13]([NH2:30])[CH:12]=3)=[N:8][CH:7]=[N:6][C:5]=2[C:4]([CH3:31])=[N:3]1.[CH3:32][CH2:33][N:34](C(C)C)C(C)C.Br[CH:42]([CH2:46][CH3:47])[C:43](Br)=[O:44].C(N)C>C1(C)C=CC=CC=1>[CH3:1][N:2]1[C:10]2[C:9]([C:11]3[CH:16]=[C:15]([C:17]#[C:18][C:19]4[CH:20]=[C:21]5[C:26](=[CH:27][CH:28]=4)[C:25]([CH3:29])=[N:24][CH:23]=[CH:22]5)[N:14]=[C:13]([NH:30][C:43](=[O:44])[CH:42]([NH:34][CH2:33][CH3:32])[CH2:46][CH3:47])[CH:12]=3)=[N:8][CH:7]=[N:6][C:5]=2[C:4]([CH3:31])=[N:3]1

Komponenten

6

Edukt 4

HCID 6341EthylamineHCID 81531DiisopropylethylamineHCID 1172932-Bromobutanoyl bromide2×HCID 1179028684-(1,3-Dimethyl-1H-pyrazolo[4,3-d]pyrimidin-7-yl)-6-((1-methylisoquinolin-6-yl)ethynyl)pyridin-2-amine

Produkt 1

HCID 117902529N-(4-{1,3-dimethyl-1H-pyrazolo[4,3-d]pyrimidin-7-yl}-6-[2-(1-methylisoquinolin-6-yl)ethynyl]pyridin-2-yl)-2-(ethylamino)butanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 4-{1,3-dimethyl-1H-pyrazolo[4,3-d]pyrimidin-7-yl}-6-[2-(1-methylisoquinolin-6-yl)ethynyl]pyridin-2-amine (30 mg, 74 μmol), toluene (200 μl) and DIPEA (57 μl, 333 μmol) is cooled to 0° C. 2-Bromobutanoyl bromide (29 μl, 0.24 mmol) in toluene (200 μl) is added dropwise. The mixture is warmed to 50° C. and stirring is continued for 16 h. Cooled to RT 2-bromobutanoyl bromide (29 μl, 0.24 mmol) in toluene (200 μl) is added dropwise. The mixture is stirred at 60° C. for 16 h before it is again cooled to RT. Ethanamine (aqueous solution 70 wt.-%, 1 ml) is added and the mixture stirred for 16 h at 80° C. The mixture is concentrated in vacuo and the product purified by RP HPLC. Yield: 3 mg (8%). HPLC-MS: M+H=519; tR=1.37 min (METHOD—1).

Aufarbeitung

  1. temperatureThe mixture is warmed to 50° C.
  2. additionis added dropwise
  3. stirringThe mixture is stirred at 60° C. for 16 h before it
  4. temperatureis again cooled to RT
  5. stirringthe mixture stirred for 16 h at 80° C
  6. concentrationThe mixture is concentrated in vacuo
  7. customthe product purified by RP HPLC

Quellen und Nachweise

ORD-Eintrag
ord-88a6499cb73e46f6a620c4d15d3506d2
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278978B2

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