p-Toluenesulfonic acid → 6-(4-Bromo-2-fluoro-phenyl)-4,5-difluoro-2-methyl-6,8-dihydro-imidazo[4',5':3,4]benzo[1,2-d]oxazol-7-one

HRID 1914879Notes

Reaction equation

HRID 1914879 reaction equation
[NH2:1][C:2]1[C:19]([F:20])=[C:18]([F:21])[C:5]2[N:6]([C:10]3[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:11]=3[F:17])[C:7](=[O:9])[NH:8][C:4]=2[C:3]=1[OH:22].[CH2:23](OC(OCC)(OCC)C)[CH3:24].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([N:6]2[C:5]3[C:18]([F:21])=[C:19]([F:20])[C:2]4[N:1]=[C:23]([CH3:24])[O:22][C:3]=4[C:4]=3[NH:8][C:7]2=[O:9])=[C:11]([F:17])[CH:12]=1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 66221Triethyl orthoacetateHCID 683137725-Amino-1-(4-bromo-2-fluoro-phenyl)-6,7-difluoro-4-hydroxy-1,3-dihydro-benzoimidazol-2-one

Product 1

HCID 672363876-(4-Bromo-2-fluoro-phenyl)-4,5-difluoro-2-methyl-6,8-dihydro-imidazo[4',5':3,4]benzo[1,2-d]oxazol-7-oneYield 54.68%

Procedure

Intermediate I-17a was prepared from 5-amino-1-(4-bromo-2-fluoro-phenyl)-6,7-difluoro-4-hydroxy-1,3-dihydro-benzoimidazol-2-one (I-14a: 600 mg, 1.6 mmol), 1,1,1-triethoxy-ethane (5 mL) and p-toluene sulfonic acid (100 mg) using procedures analogous to those described above for Intermediate I-16a to afford 350 mg of the product (54.68% yield). H1NMR (DMSO-d6, 300 MHz): δ 12.40 (s, 1H), 7.90 (dd, 1H), 7.72-7.60 (m, 2H), 2.68 (s, 3H).

Sources & evidence

ORD record
ord-a28b0c7f93b84e1696365f76cf06aa78
Source dataset
uspto-grants-2013_12
Patent number
US08614239B2

Reaction notes

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