HOAt → 2-Cyano-4-(cyclohexylmethylamino)pyrimidine-5-carboxylic acid(2-morpholin-4-yl-1-phenylethyl)amide

HRID 645491

Reaktionsgleichung

Reaktionsgleichung von HRID 645491
[C:1]([C:3]1[N:8]=[C:7]([NH:9][CH2:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:6]([C:17]([OH:19])=O)=[CH:5][N:4]=1)#[N:2].[N:20]1([CH2:26][CH:27]([NH2:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.CCN=C=NCCCN(C)C.Cl.O.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C.CCOC(C)=O>[N:20]1([CH2:26][CH:27]([NH:34][C:17]([C:6]2[C:7]([NH:9][CH2:10][CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]3)=[N:8][C:3]([C:1]#[N:2])=[N:4][CH:5]=2)=[O:19])[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

Komponenten

7

Edukt 4

HCID 181649HOAtHCID 28144622-(Morpholin-4-yl)-1-phenylethan-1-amineHCID 687033802-Cyano-4-(cyclohexylmethylamino)-pyrimidine-5-carboxylic acidHCID 87672115EDCl H2O

Produkt 1

HCID 575803772-Cyano-4-(cyclohexylmethylamino)pyrimidine-5-carboxylic acid(2-morpholin-4-yl-1-phenylethyl)amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-cyano-4-(cyclohexylmethylamino)-pyrimidine-5-carboxylic acid (0.33 mmol, step 1.4) in DMF (2.0 mL) are added 2-morpholin-4-yl-1-phenylethylamine (69 mg, step 1.3), EDCl—H2O (0.50 mmol) and HOAt (0.50 mmol) at room temperature. After stirring at room temperature for 24 h, the reaction mixture is diluted with AcOEt. The mixture is washed with water, dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residue is purified by RP-HPLC to give the title compound; 1H NMR (DMSO) δ 0.6-1.08 (m, 2H), 1.20-1.35 (m, 3H), 1.65-1.78 (m, 6H), 2.48-2.53 (m, 2H), 2.60-2.62 (m, 2H), 2.87-2.93 (m, 2H), 3.31-3.35 (m, 1H), 3.36-3.44 (M, 1H), 3.60-3.68 (m, 4H), 5.29-5.35 (m, 1H), 7.34-7.36 (m, 1H), 7.43-7.47 (m, 2H), 7.50-7.52 (m, 2H), 8.86 (s, 1H), 9.00-9.04 (m, 1H), 9.21 (d, 1H).

Aufarbeitung

  1. washThe mixture is washed with water
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue is purified by RP-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-aef23442ebd141288d5b04ce6fa32f44
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07704996B2

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