Lithium Hydroxide → Cyclopropanesulfonic acid [4,5-difluoro-6-(2-fluoro-4-bromo-phenylamino)-2-methyl-benzooxazol-7-yl]-amide

HRID 1914904Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1914904
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[C:13]([F:22])=[C:14]([F:21])[C:15]4[N:16]=[C:17]([CH3:20])[O:18][C:19]=4[C:11]=3[N:10]([S:23]([CH:26]3[CH2:28][CH2:27]3)(=[O:25])=[O:24])C2=O)=[C:4]([F:30])[CH:3]=1.[Li+].[OH-].FC1C2N=COC=2C(NS(C2CC2)(=O)=O)=C(NC2C=CC(I)=CC=2F)C=1F>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:12]2[C:13]([F:22])=[C:14]([F:21])[C:15]3[N:16]=[C:17]([CH3:20])[O:18][C:19]=3[C:11]=2[NH:10][S:23]([CH:26]2[CH2:28][CH2:27]2)(=[O:24])=[O:25])=[C:4]([F:30])[CH:3]=1

Komponenten

5

Edukt 3

HCID 3939Lithium HydroxideHCID 53241452Cyclopropanesulfonic acid [4,5-difluoro-6-(2-fluoro-4-iodo-phenylamino)-benzooxazol-7-yl]-amideHCID 672372936-(4-Bromo-2-fluoro-phenyl)-8-cyclopropanesulfonyl-4,5-difluoro-2-methyl-6,8-dihydro-imidazo [4',5':3,4]benzo[1,2-d]oxazol-7-one

Produkt 1

HCID 53241562Cyclopropanesulfonic acid [4,5-difluoro-6-(2-fluoro-4-bromo-phenylamino)-2-methyl-benzooxazol-7-yl]-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Compound 1H was prepared from 6-(4-bromo-2-fluoro-phenyl)-8-cyclopropanesulfonyl-4,5-difluoro-2-methyl-6,8-dihydro-imidazo[4′,5′:3,4]benzo[1,2-d]oxazol-7-one (I-26a: 100 mg, 0.2 mmol) and LiOH (50 mg, 1.25 mmol) in water (2 mL) using procedures analogous to those described above for Compound 1A to afford 30 mg of the product (31.57% yield). H1NMR (CDCl3, 300 MHz): δ 7.30-7.24 (m, 1H), 7.11 (dt, 1H), 6.56 (s, 1H), 6.54-6.46 (m, 1H), 6.33 (s, 1H), 2.70 (s, 3H), 2.68-2.60 (m, 1H), 1.24-1.16 (m, 2H), 1.04-0.96 (m, 2H). LCMS: 95.35%, m/z=474.0 (M-2). HPLC: 93.89%

Quellen und Nachweise

ORD-Eintrag
ord-f551a3a104384ff9929b476c81725730
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614239B2

Notizen zur Reaktion

Wird geladen…