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

HRID 1256118Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1256118
[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](O)=[O:10])[CH:7]=1.[CH2:26]([NH2:29])[CH2:27][CH3:28].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.O>CN(C=O)C>[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:29][CH2:26][CH2:27][CH3:28])=[O:10])[CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7852PropylamineHCID 2724699PyBOPHCID 53234452HCID 53234452, Verbindung

Produkt 1

HCID 673121452-(5-Amino-2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-N-propylacetamideAusbeute 51,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-(5-amino-2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)acetic acid (360 mg, 1 mmol) and n-propylamine (0.6 mL, 6 mmol) in 10 mL of DMF was added PyBOP (780 mg, 1.5 mmol) and TEA (0.5 mL, 3.56 mmol). The reaction mixture was stirred for 16 hours. After water was added, the reaction mixture was extracted with ethyl acetate and washed with water, 1N HCl and brine. The organic layer was dried over Na2SO4 and concentrated. The crude residue was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column) to give the desired product as a white powder (207 mg, yield 51%). MS calcd for (C18H22BN3O5S): 403.1. MS found (ESI negative): (M−H)−=402.1. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.89 (s, 1H), 9.17 (bs, 1H), 7.99 (t, J=5.6 Hz, 1H), 7.42 (m, 2H), 7.22 (d, J=8 Hz, 1H), 7.11 (dd, J=8, 2 Hz, 1H), 6.46 (d, J=2 Hz, 1H)), 6.35 (d, J=8.8, 2.4 Hz, 1H), 4.87 (s, 2H), 3.78 (s, 2H), 3.05 (m, 2H), 1.43 (m, 2H), 0.85 (t, J=7.2 Hz, 3H).

Aufarbeitung

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washwashed with water, 1N HCl and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude residue was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column)

Quellen und Nachweise

ORD-Eintrag
ord-7a1b649f6f964c6d849794461d4f3a65
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461134B2

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