HCID 16064600, compound → HCID 178481205, compound

HRID 1455183Notes

Reaction equation

HRID 1455183 reaction equation
[H-].COCCO[Al+]OCCOC.[Na+].[H-].C([O:17][C:18]([C:20]1[N:21]=[C:22]([C:29]2[CH:34]=[C:33]([O:35][C:36]3[CH:57]=[CH:56][C:39]4[N:40]([CH3:55])[C:41]([NH:43][C:44]5[CH:49]=[C:48]([C:50]([F:53])([F:52])[F:51])[CH:47]=[CH:46][C:45]=5[F:54])=[N:42][C:38]=4[CH:37]=3)[CH:32]=[CH:31][N:30]=2)[NH:23][C:24]=1[C:25]([F:28])([F:27])[F:26])=O)C>C1(C)C=CC=CC=1>[F:54][C:45]1[CH:46]=[CH:47][C:48]([C:50]([F:53])([F:52])[F:51])=[CH:49][C:44]=1[NH:43][C:41]1[N:40]([CH3:55])[C:39]2[CH:56]=[CH:57][C:36]([O:35][C:33]3[CH:32]=[CH:31][N:30]=[C:29]([C:22]4[NH:23][C:24]([C:25]([F:28])([F:26])[F:27])=[C:20]([CH2:18][OH:17])[N:21]=4)[CH:34]=3)=[CH:37][C:38]=2[N:42]=1

Participants

4

Reactant 2

HCID 16064600HCID 16064600, compoundHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 178481205HCID 178481205, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Red-A1 (sodium bis(2-methoxyethoxy)aluminium hydride, 65% wt in toluene, 0.1 mL) was added dropwise to a solution of 2-{4-[2-(2-fluoro-5-trifluoromethyl-phenylamino)-1-methyl-1H-benzoimidazol-5-yloxy]-pyridin-2-yl}-5-trifluoromethyl-1H-imidazole-4-carboxylic acid ethyl ester (0.0104 g, 0.017 mmol) in toluene. Effervescence was observed and after 20 min, the reaction was quenched with H2O, NaOH and extracted with EtOAc. The organic layer was washed with H2O, dried over Na2SO4, filtered and concentrated to give 5.9 mg of crude (2-{4-[2-(2-fluoro-5-trifluoromethyl-phenylamino)-1-methyl-1H-benzoimidazol-5-yloxy]-pyridin-2-yl}-5-trifluoromethyl-1H-imidazol-4-yl)-methanol which was further purified by RP HPLC (reverse phase HPLC) to give 1.1 mg of the pure compound (98% purity). LC/MS m/z 567.1 (MH+), Rt 2.40 min.

Workup

  1. customthe reaction was quenched with H2O, NaOH
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with H2O
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-21badbcbfe6a41359557262b7e3eac8e
Source dataset
uspto-grants-2009_01
Patent number
US07482367B2

Reaction notes

Loading…