HCID 178467394, compound → HCID 178467393, compound

HRID 1875223Notes

Reaction equation

HRID 1875223 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH:29]([OH:31])[CH3:30])[NH:5][C:6]=1[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18][C:19]2[CH:24]=[C:23]([C:25]#[N:26])[CH:22]=[C:21]([Cl:27])[CH:20]=2)[C:12]=1[F:28])=[O:8]>O=[Mn]=O>[C:29]([C:4]1[NH:5][C:6]([C:7]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18][C:19]3[CH:24]=[C:23]([C:25]#[N:26])[CH:22]=[C:21]([Cl:27])[CH:20]=3)[C:12]=2[F:28])=[O:8])=[C:2]([Br:1])[N:3]=1)(=[O:31])[CH3:30]

Participants

3

Reactant 1

HCID 178467394HCID 178467394, compound

Product 1

HCID 178467393HCID 178467393, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 14801Manganese dioxideCatalyst

Procedure

The title compound (0.055 g, 53%) was obtained as a white solid by MnO2 oxidation of 4-bromo-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-2-(1-hydroxyethyl)-1H-imidazole-5-carboxamide using a similar process to that described herein. 1H NMR (400 MHz, DMSO-d6) δ ppm 14.51 (br. s., 1H), 8.72-8.79 (m, 1H), 7.83 (s, 1H), 7.45-7.56 (m, 3H), 7.31-7.41 (m, 1H), 4.51 (br. s., 2H), 2.55 (s, 3 H). ES-LCMS: m/z 524.8, 526.8, 528.7 (M+1).

Sources & evidence

ORD record
ord-d558cb0dbb9044dcaa991f0344b5bbbf
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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