HCID 178509946, compound → HCID 178509945, compound

HRID 1875122Notes

Reaction equation

HRID 1875122 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([CH2:29][OH: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]>C(Cl)Cl.O1CCOCC1.O=[Mn]=O>[Cl:1][C:2]1[N:3]=[C:4]([CH:29]=[O: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]

Participants

5

Reactant 1

HCID 178509946HCID 178509946, compound

Product 1

HCID 178509945HCID 178509945, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

MnO2 (2.5 g, 29 mmol) was added to a solution of 4-chloro-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-2-(hydroxymethyl)-1H-imidazole-5-carboxamide (428 mg, 0.91 mmol) in DCM (30 mL) and 1,4-dioxane (5.0 mL). The mixture was stirred for 66 h and then the MnO2 was filtered off by through a pad of celite. Resin with 10% MeCN in DCM and the filtrates were concentrated, dried in vacuo to give the crude product (128 m, 30%) which was used for the next step without purification.

Workup

  1. filtrationthe MnO2 was filtered off by through a pad of celite
  2. concentrationResin with 10% MeCN in DCM and the filtrates were concentrated
  3. customdried in vacuo

Sources & evidence

ORD record
ord-ac955a2911154c8b9de3c4d858568db1
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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