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Piperidin-4-ol → tert-Butyl 4-[N-[7-Chloro-3-methyl-2-(4-hydroxypiperidin-1-yl)methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate

HRID 47855
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 47855
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:19])[N:7]([CH3:18])[C:8]([CH2:12]OS(C)(=O)=O)=[N:9]2)=[CH:4][C:3]=1[CH2:20][N:21]([C:25]1[CH:37]=[CH:36][C:28]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:27][CH:26]=1)[CH2:22][C:23]#[CH:24].[OH:38][CH:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1>ClCCl>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:19])[N:7]([CH3:18])[C:8]([CH2:12][N:42]3[CH2:43][CH2:44][CH:39]([OH:38])[CH2:40][CH2:41]3)=[N:9]2)=[CH:4][C:3]=1[CH2:20][N:21]([C:25]1[CH:26]=[CH:27][C:28]([C:29]([O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:30])=[CH:36][CH:37]=1)[CH2:22][C:23]#[CH:24]
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Komponenten

4

Edukt 2

HCID 79341Piperidin-4-olHCID 11813583tert-Butyl 4-[N-[7-Chloro-2-methanesulphonyloxymethyl-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate

Produkt 1

HCID 11734327tert-Butyl 4-[N-[7-Chloro-3-methyl-2-(4-hydroxypiperidin-1-yl)methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

To a solution of tert-butyl 4-[N-[7-chloro-2-methanesulphonyloxymethyl-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate (0.230 g, 0.42 mmol) in anhydrous dichloromethane (4 ml) under argon was added a solution of 4-hydroxypiperidine (0.424 g, 4.2 mmol) in anhydrous CH2Cl2 (4 ml). The clear solution was stirred at room temperature for 1.5 hours under argon, then partitioned between ethyl acetate (200 ml) and 5% aqueous sodium carbonate solution (100 ml). The organic layer was washed with 5% aqueous sodium carbonate (100 ml), and dilute brine (100 ml), dried (Na2SO4) and concentrated in vacuo. The residue was triturated with ether to give a white precipitate, which was collected by filtration , washed with ether and dried in vacuo over P2O5 (0.206 g, 89%), mp 208-210° C.; 1H-NMR (DMSO-d6) 1.50 (s, 9H, But), 1.33 (m, 2H), 1.65 (m, 2H), 2.17 (m, 2H), 2.72 (m, 2H), and 3.50 (m, 1H), (piperidine ring protons), 3.24 (s, 1H, C≡CH), 3.57, 3.60 (2×s, 5H, N3-Me , 2-CH2), 4.39 (s, 2H, CH2C≡C), 4.55 (d, J=4.1 Hz, 1H, OH), 4.79 (s, 2H, 6-CH2), 6.78 (d, J=8.9 Hz, 2H, 3′,5′-ArH), 7.72 (d, J=8.9 Hz, 2′,6′-ArH), 7.81, 7.87 (2×s, 2H, 5-H, 8-H); MS (ESI, m/z) 551, 553 [(M+H)+, 100%, 37% rcspectively; Cl isotopic pattern].

Aufarbeitung

  1. custompartitioned between ethyl acetate (200 ml) and 5% aqueous sodium carbonate solution (100 ml)
  2. washThe organic layer was washed with 5% aqueous sodium carbonate (100 ml), and dilute brine (100 ml)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with ether
  6. customto give a white precipitate, which
  7. filtrationwas collected by filtration
  8. washwashed with ether
  9. dry with materialdried in vacuo over P2O5 (0.206 g, 89%), mp 208-210° C.

Quellen und Nachweise

ORD-Eintrag
ord-e21bccf40f5b4785a2317b95e05a06c2
Quelldatensatz
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06699861B1

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