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Benzaldehyde → HCID 9893125, Verbindung

HRID 1760418
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1760418
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]([C:21]1[CH:26]=[C:25]([CH3:27])[N:24]=[C:23]([N:28]2[CH:32]=[CH:31][N:30]=[CH:29]2)[N:22]=1)[CH2:6][C:7]([NH:9][CH2:10][CH2:11][C:12]1[CH:20]=[CH:19][C:15]2[O:16][CH2:17][O:18][C:14]=2[CH:13]=1)=[O:8].[CH:33](=O)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.N1C=CC=CC=1.B>CO>[C:34]1([CH2:33][NH:1][CH2:2][CH2:3][CH2:4][N:5]([C:21]2[CH:26]=[C:25]([CH3:27])[N:24]=[C:23]([N:28]3[CH:32]=[CH:31][N:30]=[CH:29]3)[N:22]=2)[CH2:6][C:7]([NH:9][CH2:10][CH2:11][C:12]2[CH:20]=[CH:19][C:15]3[O:16][CH2:17][O:18][C:14]=3[CH:13]=2)=[O:8])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1
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Komponenten

5

Edukt 3

HCID 240BenzaldehydeHCID 2723995Borane;pyridineHCID 99109492-[(3-aminopropyl)[2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino]-N-[2-(1,3-benzodioxol-5-yl)ethyl]acetamide

Produkt 1

HCID 9893125HCID 9893125, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To 2-[(3-aminopropyl)[2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino]-N-[2-(1,3-benzodioxol-5-yl)ethyl]acetamide (50 mg, 0.11 mmol) (a compound of formula (Yc6)) in methanol (2 mL) was added benzaldehyde (0.2 M in methanol, 68 μL, 0.14 mmol). After stirring for 15 minutes, borane-pyridine complex (0.2 M in methanol, 0.14 mmol) was added. After 2 hours, the solution was evaporated. The residue was partitioned into water and ethyl acetate. The aqueous layer was extracted twice with ethyl acetate. The combined ethyl acetate fractions were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (2:1 ethyl acetate/hexanes) to provide 2-[[3-(phenylmethylamino)propyl][2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino]-N-[2-(1,3-benzodioxol-5-yl)ethyl]acetamide, a compound of formula (Yc8); as a white solid; NMR (CDCl3) 8.65 (s, 1), 7.7 (s, 1), 7.2 (br, 5), 7.1 (s, 1), 6.6 (d, 1), 6.55 (s, 1), 6.5 (d, 1), 6.1 (br, 2), 5.9 (s, 2), 3.95 (br, 2), 3.5 (br, 6), 2.7 (m, 3), 2.35 (s, 6) ppm.

Aufarbeitung

  1. waitAfter 2 hours
  2. customthe solution was evaporated
  3. customThe residue was partitioned into water and ethyl acetate
  4. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. washThe combined ethyl acetate fractions were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel (2:1 ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-fa03a216dc0643cebc27e7e3f7898a90
Quelldatensatz
uspto-grants-2005_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06841674B2

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