Cyclohexylamine → 2-(5-Amino-2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-N-cyclohexylacetamide

HRID 1256126Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1256126
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:12](=[O:25])(=[O:24])[NH:13][C:14]2[CH:15]=[CH:16][C:17]3[CH2:21][O:20][B:19]([OH:22])[C:18]=3[CH:23]=2)=[C:6]([CH2:8][C:9]([OH:11])=O)[CH:7]=1.[CH:26]1([NH2:32])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:12](=[O:24])(=[O:25])[NH:13][C:14]2[CH:15]=[CH:16][C:17]3[CH2:21][O:20][B:19]([OH:22])[C:18]=3[CH:23]=2)=[C:6]([CH2:8][C:9]([NH:32][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[O:11])[CH:7]=1

Komponenten

7

Edukt 4

HCID 7965CyclohexylamineHCID 8471TriethylamineHCID 2724699PyBOPHCID 53234452HCID 53234452, Verbindung

Produkt 1

HCID 673125302-(5-Amino-2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-N-cyclohexylacetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To the mixture of 2-(5-amino-2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)acetic acid (1.09 g, 3 mmol) and cyclohexyl amine (1.4 ml, 12 mmol) in DMF (10 ml), added PyBOP (1.56 g, 3 mmol) then triethyl amine (0.4 ml, 3 mmol). Stirring was kept for 3 hours. Diluted with EtOAc, washed with 1N HCl, water and brine. Dried over anhydrous sodium sulfate. Concentrated, the residue was dissolved in DMSO and purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column). The title compound was obtained as light yellow powder. MS calcd for (C21H26BN3O5S): 443.17. MS found (ESI negative): (M−H)−=442.2. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.87 (s, 1H), 7.90 (d, J=6 Hz, 1H), 7.41 (s, 1H), 7.39 (d, J=8.8 Hz, 1H), 7.20 (d, J=8 Hz, 1H), 7.08 (dd, J=8 Hz, 1H), 6.45 (d, J=2 Hz, 1H), 6.33 (dd, J=8.8 Hz, 1H), 4.85 (s, 2H), 3.75 (s, 2H), 3.55 (m, 1H), 1.80-1.50 (m, 5H), 1.30-1.10 (m, 5H).

Aufarbeitung

  1. washwashed with 1N HCl, water and brine
  2. dry with materialDried over anhydrous sodium sulfate
  3. concentrationConcentrated
  4. dissolutionthe residue was dissolved in DMSO
  5. custompurified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column)

Quellen und Nachweise

ORD-Eintrag
ord-62ea8b2b3eb645389ef774365e642126
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461134B2

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