Cyanoacetic acid → 3-(4-(2-(4-(4-Acetylpiperazin-1-yl)phenylamino)-5-fluoropyrimidin-4-yl)piperazin-1-yl)-3-oxopropanenitrile

HRID 2281542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2281542
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].C(Cl)(=O)C(Cl)=O.[F:13][C:14]1[C:15]([N:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)=[N:16][C:17]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:32][CH2:31][N:30]([C:33](=[O:35])[CH3:34])[CH2:29][CH2:28]3)=[CH:23][CH:22]=2)=[N:18][CH:19]=1>C(Cl)Cl.CN(C=O)C>[C:33]([N:30]1[CH2:31][CH2:32][N:27]([C:24]2[CH:25]=[CH:26][C:21]([NH:20][C:17]3[N:16]=[C:15]([N:36]4[CH2:37][CH2:38][N:39]([C:4](=[O:6])[CH2:3][C:1]#[N:2])[CH2:40][CH2:41]4)[C:14]([F:13])=[CH:19][N:18]=3)=[CH:22][CH:23]=2)[CH2:28][CH2:29]1)(=[O:35])[CH3:34]

Komponenten

6

Edukt 3

HCID 9740Cyanoacetic acidHCID 65578Oxalyl chlorideHCID 444671001-(4-(4-(5-Fluoro-4-(piperazin-1-yl)pyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone

Produkt 1

HCID 444673163-(4-(2-(4-(4-Acetylpiperazin-1-yl)phenylamino)-5-fluoropyrimidin-4-yl)piperazin-1-yl)-3-oxopropanenitrileAusbeute 63,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a suspension of cyanoacetic acid (85 mg, 1.00 mmol) in CH2Cl2 (2 mL) (containing 2 drops of DMF) at room temperature, oxalyl chloride (0.082 mL, 0.94 mmol) was added. Gas evolved and suspension became clear. It was then stirred for 50 min. To the above solution cooled in an ice bath, a solution of 1-(4-(4-(5-fluoro-4-(piperazin-1-yl)pyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone (23 mg, 0.057 mmol) and TEA (0.400 mL, 2.87 mmol) in DMF (1 mL) was added drop wise. The mixture was then stirred at room temperature for 90 min. It was concentrated in vacuo. The residue was purified by HPLC to give the titled compound (17 mg). MS 467.5 (M+H); UV 201.0, 269.4 nm

Aufarbeitung

  1. temperatureTo the above solution cooled in an ice bath
  2. stirringThe mixture was then stirred at room temperature for 90 min
  3. concentrationIt was concentrated in vacuo
  4. customThe residue was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-e70ba57cd58a45f6bf73c387f50a8139
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139581B2

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