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2-Pyridinemethanamine → 1-(5-(5-Phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)pyridin-3-yl)ethane-1,2-diol

HRID 593712
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 593712
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5]([C:18]2[CH:19]=[N:20][CH:21]=[C:22]([CH:24]3[CH2:28][O:27]C(C)(C)[O:25]3)[CH:23]=2)=[N:4][N:3]=1.[N:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH2:37][NH2:38]>C1(C)C=CC=CC=1.C(Cl)Cl>[C:12]1([C:10]2[CH:9]=[CH:8][CH:7]=[C:6]3[C:11]=2[C:2]([NH:38][CH2:37][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][N:31]=2)=[N:3][N:4]=[C:5]3[C:18]2[CH:23]=[C:22]([CH:24]([OH:25])[CH2:28][OH:27])[CH:21]=[N:20][CH:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 195092-PyridinemethanamineHCID 904245884-Chloro-1-(5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridin-3-yl)-5-phenylphthalazine

Produkt 1

HCID 862702951-(5-(5-Phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)pyridin-3-yl)ethane-1,2-diolAusbeute 5,11 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel
HCID 6344
Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 4-chloro-1-(5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridin-3-yl)-5-phenylphthalazine (1.00 g, 2.39 mmol) in toluene (5 mL) was added pyridin-2-ylmethanamine (5.00 mL, 48.5 mmol) the contents were heated at 100° C. for 12 h. The reaction mixture was diluted with DCM (200 mL) and washed with 1.5N HCl (2 ×20 mL). The organic extract was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The resulting crude was purified by preparative HPLC (Condition 18 as described in general methods) to obtain 1-(5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)pyridin-3-yl)ethane-1,2-diol (55.0 mg, 5.11%) as a white solid. The racemic product (50 mg) was resolved into individual enantiomers by chiral SFC (Condition 29 as described in general methods).

Aufarbeitung

  1. washwashed with 1.5N HCl (2 ×20 mL)
  2. extractionThe organic extract
  3. dry with materialwas dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting crude was purified by preparative HPLC (Condition 18 as described in general methods)

Quellen und Nachweise

ORD-Eintrag
ord-8bff044100bd440986ae462af654f76a
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09242966B2

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