HCID 66792166, compound → HCID 58487847, compound

HRID 1406388Notes

Reaction equation

HRID 1406388 reaction equation
[OH:1][CH:2]([C:4]1[CH:32]=[CH:31][C:7]([O:8][C:9]2[CH:30]=[CH:29][C:12]([CH2:13][NH:14][C:15]([C:17]3([NH:20][C:21]([C:23]4[CH:24]=[N:25][CH:26]=[N:27][CH:28]=4)=[O:22])[CH2:19][CH2:18]3)=[O:16])=[CH:11][CH:10]=2)=[C:6]([C:33]([F:36])([F:35])[F:34])[CH:5]=1)[CH3:3]>ClCCl.[O-2].[O-2].[Mn+4]>[C:2]([C:4]1[CH:32]=[CH:31][C:7]([O:8][C:9]2[CH:30]=[CH:29][C:12]([CH2:13][NH:14][C:15]([C:17]3([NH:20][C:21]([C:23]4[CH:28]=[N:27][CH:26]=[N:25][CH:24]=4)=[O:22])[CH2:19][CH2:18]3)=[O:16])=[CH:11][CH:10]=2)=[C:6]([C:33]([F:34])([F:35])[F:36])[CH:5]=1)(=[O:1])[CH3:3]

Participants

4

Reactant 1

HCID 66792166HCID 66792166, compound

Product 1

HCID 58487847HCID 58487847, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 70 mg (0.14 mmol) of pyrimidine-5-carboxylic acid(1-{4-[4-(1-hydroxyethyl)-2-trifluoromethyl-phenoxy]-benzylcarbamoyl}-cyclopropyl)amide (product from Example 153) in 10 mL dichloromethane was combined with 300 mg (3.5 mmol) of manganese dioxide and stirred for three days at ambient temperature. The mixture was then filtered and evaporated down. The crude product thus obtained was purified by chromatography (reversed phase HPLC).

Workup

  1. filtrationThe mixture was then filtered
  2. customevaporated down

Sources & evidence

ORD record
ord-59986820f8fb4c0da12c1365b149b1ab
Source dataset
uspto-grants-2014_12
Patent number
US08916589B2

Reaction notes

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