Dichloromethane → N-Hydroxy 2-(6-{(naphthalene-2-sulfonyl)-[2-(2-oxopyrrolidin-1-yl)ethyl]amino}-3-aza-bicyclo[3.1.0]hex-3-yl)pyrimidine-5-carboxamide

HRID 2079792

Reaktionsgleichung

Reaktionsgleichung von HRID 2079792
C(OC([O:8][NH:9][C:10]([C:12]1[CH:13]=[N:14][C:15]([N:18]2[CH2:23][CH:22]3[CH:20]([CH:21]3[N:24]([S:33]([C:36]3[CH:45]=[CH:44][C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[CH:37]=3)(=[O:35])=[O:34])[CH2:25][CH2:26][N:27]3[CH2:31][CH2:30][CH2:29][C:28]3=[O:32])[CH2:19]2)=[N:16][CH:17]=1)=[O:11])C)C(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl>CO>[OH:8][NH:9][C:10]([C:12]1[CH:17]=[N:16][C:15]([N:18]2[CH2:19][CH:20]3[CH:22]([CH:21]3[N:24]([S:33]([C:36]3[CH:45]=[CH:44][C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[CH:37]=3)(=[O:35])=[O:34])[CH2:25][CH2:26][N:27]3[CH2:31][CH2:30][CH2:29][C:28]3=[O:32])[CH2:23]2)=[N:14][CH:13]=1)=[O:11]

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 59367679N-(1-isobutoxyethoxy) 2-(6-{(naphthalene-2-sulfonyl)-[2-(2-oxopyrrolidin-1-yl)ethyl]amino}-3-azabicyclo[3.1.0]hex-3-yl)pyrimidine-5-carboxamide

Produkt 1

HCID 59367598N-Hydroxy 2-(6-{(naphthalene-2-sulfonyl)-[2-(2-oxopyrrolidin-1-yl)ethyl]amino}-3-aza-bicyclo[3.1.0]hex-3-yl)pyrimidine-5-carboxamideAusbeute 11 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To N-(1-isobutoxyethoxy) 2-(6-{(naphthalene-2-sulfonyl)-[2-(2-oxopyrrolidin-1-yl)ethyl]amino}-3-azabicyclo[3.1.0]hex-3-yl)pyrimidine-5-carboxamide was added TFA:DCM:MeOH (3.5 ml, 1:2:2 mixture). The solution was stirred overnight, and then concentrated in vacuo. The product was purified by reverse phase HPLC to yield the title compound as a white solid (18 mg, 11%). LCMS Purity >98%, m/z 537 [M+H]+, 1H NMR (300 MHz, d6-DMSO) 1.83-1.95 (3H, m), 2.17 (2H, t, J=8.2 Hz), 2.22-2.26 (2H, m), 3.36-3.45 (6H, m), 3.52-3.59 (2H, m), 3.79 (2H, t, J=11.8 Hz), 7.66-7.76 (2H, m), 7.83 (1H, dd, J=1.8, 8.7 Hz), 8.04-8.09 (1H, m), 8.18 (1H, d, J=8.8 Hz), 8.22-8.27 (1H, m), 8.53-8.56 (1H, m), 8.63 (2H, s), 8.99 (1H, br s), 11.03 (1H, br s).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customThe product was purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-39988f2f35764d3cbb0f9a3b2b6db405
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932246B2

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