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Formaldehyde → 2-Cyano-4-[2-(1-methylpiperidin-4-yl)ethoxy]-6-[(spiro[2.5]oct-6-ylmethyl)amino]pyrimidine-5-carboxylic acid benzylamide

HRID 645518
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Reaktionsgleichung

Reaktionsgleichung von HRID 645518
[CH2:1]([NH:8][C:9]([C:11]1[C:12]([O:29][CH2:30][CH2:31][CH:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)=[N:13][C:14]([C:27]#[N:28])=[N:15][C:16]=1[NH:17][CH2:18][CH:19]1[CH2:26][CH2:25][C:22]2([CH2:24][CH2:23]2)[CH2:21][CH2:20]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[BH3-][C:41]#N.[Na+]>C1COCC1>[CH2:1]([NH:8][C:9]([C:11]1[C:12]([O:29][CH2:30][CH2:31][CH:32]2[CH2:37][CH2:36][N:35]([CH3:41])[CH2:34][CH2:33]2)=[N:13][C:14]([C:27]#[N:28])=[N:15][C:16]=1[NH:17][CH2:18][CH:19]1[CH2:20][CH2:21][C:22]2([CH2:23][CH2:24]2)[CH2:25][CH2:26]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 68708606HCID 68708606, Verbindung

Produkt 1

HCID 445873662-Cyano-4-[2-(1-methylpiperidin-4-yl)ethoxy]-6-[(spiro[2.5]oct-6-ylmethyl)amino]pyrimidine-5-carboxylic acid benzylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel
2×

Versuchsvorschrift

To a solution of 2-cyano-4-(2-piperidin-4-yl-ethoxy)-6-[(spiro[2.5]oct-6-ylmethyl)amino]-pyrimidine-5-carboxylic acid benzylamide (0.19 mmol) in THF (2 mL) is added formaldehyde solution (100 μL), and the resulting solution is stirred for 0.5 h at room temperature. After cooled to 0° C., 1 M NaBH3CN solution in THF is added dropwise, and the reaction mixture is stirred for 2 h at room temperature. The reaction is quenched by the addition of H2O, and extracted twice with AcOEt. The organic layer is dried over Na2SO4, filtered, and concentrated. The residue is purified by silica gel column to give 2-cyano-4-[2-(1-methylpiperidin-4-yl)ethoxy]-6-[(spiro[2.5]oct-6-ylmethyl)amino]pyrimidine-5-carboxylic acid benzylamide as a colorless oil; 1H-NMR (CDCl3), δ 0.17-0.30 (4H, m), 0.89-0.94 (2H, m), 1.14-1.29 (3H, m), 1.40-1.50 (2H, m), 1.58-1.78 (9H, m), 1.95-2.01 (3H, m), 2.38 (3H, s), 2.95-2.98 (2H, m), 3.42 (2H, t), 4.46 (2H, t), 4.56 (2H, d), 7.31-7.39 (5H, m), 8.13 (1H, t), 10.16 (1H, t).

Aufarbeitung

  1. temperatureAfter cooled to 0° C.
  2. stirringthe reaction mixture is stirred for 2 h at room temperature
  3. customThe reaction is quenched by the addition of H2O
  4. extractionextracted twice with AcOEt
  5. dry with materialThe organic layer is dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is purified by silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-51b0533e64184cd6a15288601653e68c
Quelldatensatz
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07704996B2

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