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Acetic Acid → 2-((2-Chloro-5-cyano-3-(4-ethyl-2-oxopiperazin-1-yl)phenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

HRID 921886
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 921886
[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][C:9]2=[O:14])=[CH:6][C:5]([C:15]#[N:16])=[CH:4][C:3]=1[NH:17][C:18]1[N:23]=[C:22]([N:24]([CH:34]2[CH2:36][CH2:35]2)CC2C=CC(OC)=CC=2)[C:21]2=[N:37][CH:38]=[C:39]([C:40]#[N:41])[N:20]2[N:19]=1.[CH:42](=O)[CH3:43].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(C(F)(F)F)=O>C(Cl)Cl.ClCCCl.C1(OC)C=CC=CC=1>[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH2:42][CH3:43])[CH2:10][C:9]2=[O:14])=[CH:6][C:5]([C:15]#[N:16])=[CH:4][C:3]=1[NH:17][C:18]1[N:23]=[C:22]([NH:24][CH:34]2[CH2:36][CH2:35]2)[C:21]2=[N:37][CH:38]=[C:39]([C:40]#[N:41])[N:20]2[N:19]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 6422Trifluoroacetic acidHCID 5049666Sodium triacetoxyborohydrideHCID 899226992-((2-Chloro-5-cyano-3-(2-oxopiperazin-1-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

Produkt 1

HCID 89923411
2-((2-Chloro-5-cyano-3-(4-ethyl-2-oxopiperazin-1-yl)phenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile
Ausbeute 69,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 7519AnisoleKatalysatorHCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 2-((2-chloro-5-cyano-3-(2-oxopiperazin-1-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (17 mg, 0.030 mmol) in DCM (2 mL) was added acetaldehyde (13.16 mg, 0.299 mmol) and acetic acid (3.42 μl, 0.060 mmol). After stirring for 15 min, sodium triacetoxyborohydride (12.66 mg, 0.060 mmol) was added. After stirring at room temperature for 2 h, LC-MS indicated completion. After concentration, purification via flash chromatography (0-10% MeOH in DCM, 12 g) gave 20 mg of the PMB protected product. This was dissolved in 1 mL of DCE and then 1 drop of anisole was added followed by 0.5 mL of TFA. The solution was heated at 60° C. for 2.5 h. LC-MS indicated completion, and then it was cooled and concentrated. The crude was dissolved in methanol and neutralized with 7N ammonia in methanol. After stirring for 10 min it was concentrated, purification via preparative HPLC gave the title compound as a yellow solid (10 mg).

Aufarbeitung

  1. stirringAfter stirring at room temperature for 2 h
  2. concentrationAfter concentration, purification via flash chromatography (0-10% MeOH in DCM, 12 g)
  3. customgave 20 mg of the PMB
  4. temperatureit was cooled
  5. concentrationconcentrated
  6. dissolutionThe crude was dissolved in methanol and neutralized with 7N ammonia in methanol
  7. stirringAfter stirring for 10 min it
  8. concentrationwas concentrated
  9. custompurification via preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-1442195f389c449483750a0769ab1e5c
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09273057B2

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