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

HRID 1914880Notes

Reaction equation

HRID 1914880 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]([I:16])=[CH:12][C:11]=3[F:17])[C:7](=[O:9])[NH:8][C:4]=2[C:3]=1[OH:22].[C:23]1(C)C=CC(S(O)(=O)=O)=C[CH:24]=1>C(OC(OCC)(OCC)C)C>[F:20][C:19]1[C:2]2[N:1]=[C:23]([CH3:24])[O:22][C:3]=2[C:4]2[NH:8][C:7](=[O:9])[N:6]([C:10]3[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:11]=3[F:17])[C:5]=2[C:18]=1[F:21]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 68313323HCID 68313323, compound

Product 1

HCID 672384834,5-Difluoro-6-(2-fluoro-4-iodo-phenyl)-2-methyl-6,8-dihydro-imidazo[4',5':3,4]benzo[1,2-d]oxazol-7-oneYield 535.7%

Reagents, catalysts & solvents 1

HCID 66221Triethyl orthoacetateSolvent

Procedure

Intermediate I-18a was prepared from 5-amino-6,7-difluoro-1-(2-fluoro-4-iodo-phenyl)-4-hydroxy-1,3-dihydro-benzoimidazol-2-one (I-13a: 550 mg, 1.3 mmol) in 1,1,1-triethoxy-ethane (5 mL) and p-toluene sulfonic acid (20 mg, 0.13 mmol) using procedures analogous to those described above for Intermediate I-16a to afford 310 mg of the product (53.6% yield). H1NMR (DMSO-d6, 300 MHz): δ 12.39 (s, 1H), 7.96 (dd, 1H), 7.78 (d, 1H), 7.48 (t, 1H), 2.67 (s, 3H). LCMS: 92.6%, m/z=445.9 (M+1).

Sources & evidence

ORD record
ord-83c5b206e7444b7aa01610e67f83c9a2
Source dataset
uspto-grants-2013_12
Patent number
US08614239B2

Reaction notes

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