Diisopropylethylamine → N-(1-cyanoethyl)-2-(4-((4-((2,4,6-trifluorobenzyl)amino)pyrimidin-2-yl)amino)-1H-pyrazol-1-yl)acetamide

HRID 929925Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 929925
[F:1][C:2]1[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([F:27])[C:3]=1[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([NH:12][C:13]2[CH:14]=[N:15][N:16]([CH2:18][C:19](O)=[O:20])[CH:17]=2)[N:7]=1.CCN(C(C)C)C(C)C.Cl.[NH2:38][CH:39]([CH3:42])[C:40]#[N:41].CCCP(=O)=O>CN(C=O)C>[C:40]([CH:39]([NH:38][C:19](=[O:20])[CH2:18][N:16]1[CH:17]=[C:13]([NH:12][C:8]2[N:7]=[C:6]([NH:5][CH2:4][C:3]3[C:2]([F:1])=[CH:25][C:24]([F:26])=[CH:23][C:22]=3[F:27])[CH:11]=[CH:10][N:9]=2)[CH:14]=[N:15]1)[CH3:42])#[N:41]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 127828772-Aminopropanenitrile hydrochlorideHCID 16167369Propylphosphoric anhydrideHCID 900240572-(4-((4-((2,4,6-trifluorobenzyl)amino)pyrimidin-2-yl)amino)-1H-pyrazol-1-yl)acetic acid

Produkt 1

HCID 72706527N-(1-cyanoethyl)-2-(4-((4-((2,4,6-trifluorobenzyl)amino)pyrimidin-2-yl)amino)-1H-pyrazol-1-yl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2-(4-((4-((2,4,6-trifluorobenzyl)amino)pyrimidin-2-yl)amino)-1H-pyrazol-1-yl)acetic acid I-2 (0.1 g, 0.26 mmol, prepared by Procedure B), DIPEA (0.15 mL, 0.8 mmol), 2-aminopropanenitrile hydrochloride (34 mg, 0.3 mmol), propylphosphonic anhydride solution (50% in DMF) (0.17 g, 0.5 mmol) in DMF was stirred overnight at room temperature then extracted into water and washed with DCM. The aqueous layer was neutralised with aqueous sodium bicarbonate and extracted with three times with DCM. The combined organic layer was concentrated in vacuo and purified by prep. HPLC to afford N-(1-cyanoethyl)-2-(4-((4-((2,4,6-trifluorobenzyl)amino)pyrimidin-2-yl)amino)-1H-pyrazol-1-yl)acetamide I-5 (80 mg, 0.18 mmol). LC-MS (Method B), RT=5.15 min. (ES+) 431.

Aufarbeitung

  1. extractionthen extracted into water
  2. washwashed with DCM
  3. extractionextracted with three times with DCM
  4. concentrationThe combined organic layer was concentrated in vacuo
  5. custompurified by prep

Quellen und Nachweise

ORD-Eintrag
ord-e0a67e47a6234443b38058d7d8206636
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296725B2

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