HCID 16064600, compound → HCID 178481205, compound

HRID 499983Notes

Reaction equation

HRID 499983 reaction equation
COCCO[AlH2-]OCCOC.[Na+].C([O:15][C:16]([C:18]1[N:19]=[C:20]([C:27]2[CH:32]=[C:31]([O:33][C:34]3[CH:55]=[CH:54][C:37]4[N:38]([CH3:53])[C:39]([NH:41][C:42]5[CH:47]=[C:46]([C:48]([F:51])([F:50])[F:49])[CH:45]=[CH:44][C:43]=5[F:52])=[N:40][C:36]=4[CH:35]=3)[CH:30]=[CH:29][N:28]=2)[NH:21][C:22]=1[C:23]([F:26])([F:25])[F:24])=O)C>C1(C)C=CC=CC=1>[F:52][C:43]1[CH:44]=[CH:45][C:46]([C:48]([F:51])([F:50])[F:49])=[CH:47][C:42]=1[NH:41][C:39]1[N:38]([CH3:53])[C:37]2[CH:54]=[CH:55][C:34]([O:33][C:31]3[CH:30]=[CH:29][N:28]=[C:27]([C:20]4[NH:21][C:22]([C:23]([F:26])([F:24])[F:25])=[C:18]([CH2:16][OH:15])[N:19]=4)[CH:32]=3)=[CH:35][C:36]=2[N:40]=1

Participants

4

Reactant 2

HCID 16064600HCID 16064600, compoundHCID 16684438Red-Al

Product 1

HCID 178481205HCID 178481205, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Red-Al (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). LCMS 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-d7ada822effc462188f5cf0de4f56677
Source dataset
uspto-grants-2010_08
Patent number
US07767820B2

Reaction notes

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