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1-Hydroxybenzotriazole → N-({4'-[({1-[(hydroxyamino)carbonyl]-2-methylpropyl}amino)sulfonyl]biphenyl-3-yl}methyl)-4-oxo-3,4-dihydroquinazoline-2-carboxamide

HRID 606429
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Reaktionsgleichung

Reaktionsgleichung von HRID 606429
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([NH:14][CH2:15][C:16]2[CH:17]=[C:18]([C:22]3[CH:27]=[CH:26][C:25]([S:28]([NH:31][C@H:32]([C:36](O)=[O:37])[CH:33]([CH3:35])[CH3:34])(=[O:30])=[O:29])=[CH:24][CH:23]=3)[CH:19]=[CH:20][CH:21]=2)=[O:13])[NH:3]1.C[Si](C)(C)[O:41][NH2:42].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C=O)C.C(OCC)(=O)C>[OH:41][NH:42][C:36]([CH:32]([NH:31][S:28]([C:25]1[CH:26]=[CH:27][C:22]([C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([CH2:15][NH:14][C:12]([C:4]3[NH:3][C:2](=[O:1])[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:5]=3)=[O:13])[CH:17]=2)=[CH:23][CH:24]=1)(=[O:29])=[O:30])[CH:33]([CH3:34])[CH3:35])=[O:37]
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Komponenten

7

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734666O-(Trimethylsilyl)hydroxylamineHCID 136380958N-{[3'-({[(4-oxo-3,4-dihydroquinazolin-2-yl)carbonyl]amino}methyl)biphenyl-4-yl]sulfonyl}valine

Produkt 1

HCID 136054465
N-({4'-[({1-[(hydroxyamino)carbonyl]-2-methylpropyl}amino)sulfonyl]biphenyl-3-yl}methyl)-4-oxo-3,4-dihydroquinazoline-2-carboxamide
Ausbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of N-{[3′-({[(4-oxo-3,4-dihydroquinazolin-2-yl)carbonyl]amino}methyl)biphenyl-4-yl]sulfonyl}valine obtained in Example 77 (0.080 g, 0.150 mmol), O-(trimethylsilyl)hydroxylamine (0.055 mL, 0.449 mmol), 1-[3-(dimethylamino)propyl]-3-ethyl-carbodiimide hydrochloride (0.086 g, 0.449 mmol) and 1-hydroxybenzotriazole (0.061 g, 0.449 mmol) in DMF (5 mL) was stirred at room temperature for 12 hr. The reaction mixture was diluted with ethyl acetate, and washed successively with 0.05N hydrochloric acid, aqueous sodium hydrogencarbonate solution, water and saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was crystallized from methanol-diethyl ether to give the title compound as a white powder (0.058 g, 71%).

Aufarbeitung

  1. washwashed successively with 0.05N hydrochloric acid, aqueous sodium hydrogencarbonate solution, water and saturated brine
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was crystallized from methanol-diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-6a97e04b1c1e46fda93631a6ca2fbde6
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07915267B2

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