Aluminium lithium hydride → HCID 178426558, compound

HRID 1514983Notes

Reaction equation

HRID 1514983 reaction equation
C[O:2][C:3](=O)[CH2:4][NH:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13]2[NH:17][C:16]3[CH:18]=[CH:19][C:20]([C:22](=[O:32])[NH:23][C:24]4[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([CH3:31])[CH:25]=4)=[CH:21][C:15]=3[N:14]=2)=[C:8]([CH3:33])[CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:31][C:26]1[CH:25]=[C:24]([NH:23][C:22]([C:20]2[CH:19]=[CH:18][C:16]3[NH:17][C:13]([C:9]4[C:8]([CH3:33])=[CH:7][C:6]([NH:5][CH2:4][CH2:3][OH:2])=[CH:11][C:10]=4[CH3:12])=[N:14][C:15]=3[CH:21]=2)=[O:32])[CH:29]=[CH:28][C:27]=1[CH3:30]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178501558HCID 178501558, compound

Product 1

HCID 178426558HCID 178426558, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {4-[5-(3,4-dimethylphenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethylphenylamino}-acetic acid methyl ester (80 mg) in THF (5 mL), cooled at 0° C. in an ice bath, was added LiAlH4 (1M in THF, 0.26 mL) dropwise. The mixture was warmed to room temperature. After 1 hr, the reaction was quenched with 2 drops of water and filtered. The organic layer was dried, filtered and concentrated. The residue was purified by flash chromatography using hexanes/ethyl acetate (1:4) to afford 2-[4-(2-hydroxyethylamino)-2,6-dimethylphenyl]-1H-benzoimidazole-5-carboxylic acid (3,4-dimethyl-phenyl)-amide as a light yellow solid. MS (ESI)m/z 429 (M+H). 1H NMR (MeOD, 400 MHz) δ 8.20 (s, 1H), 7.87 (dd, 1H), 7.67 (s, 1H), 7.48 (d, 1H), 7.43 (dd, 1H), 7.13 (d, 1H), 6.47 (s, 2H), 3.74 (t, 2H), 3.27 (t, 2H), 2.30 (s, 3H), 2.26 (s, 3H), 2.09 (s, 6H).

Workup

  1. customthe reaction was quenched with 2 drops of water
  2. filtrationfiltered
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-7dadfbff1556470fb209f32329b07e60
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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