Pentane → 3-{4-Chloro-2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazol-7-yl}-2,4-dimethylpentan-3-ol

HRID 1698581Notes

Reaction equation

HRID 1698581 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][C:12]3[C:17]([CH3:18])=[CH:16][C:15]([Cl:19])=[CH:14][C:13]=3[O:20][CH3:21])[N:7]([CH3:22])[C:6]=2[C:5]([C:23]([O:25]C)=O)=[CH:4][CH:3]=1.CC[CH2:29][CH2:30][CH3:31].[CH:32]([Li])([CH3:34])[CH3:33]>C(OCC)C>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][C:12]3[C:17]([CH3:18])=[CH:16][C:15]([Cl:19])=[CH:14][C:13]=3[O:20][CH3:21])[N:7]([CH3:22])[C:6]=2[C:5]([C:23]([OH:25])([CH:30]([CH3:29])[CH3:31])[CH:32]([CH3:34])[CH3:33])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8003PentaneHCID 67273388Methyl 4-chloro-2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazole-7-carboxylateHCID 178506895HCID 178506895, compound

Product 1

HCID 580123753-{4-Chloro-2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazol-7-yl}-2,4-dimethylpentan-3-olYield 68%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 4-chloro-2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazole-7-carboxylate (200 mg, 0.50 mmol) in diethylether (3 mL) was added dropwise a pentane solution of isopropyl lithium (0.7 M solution, 5 mL) at −78° C., and stirred at 0° C. for 1 h. The reaction mixture was quenched with 6N hydrochloric acid, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by preparative HPLC eluting with a 5-95% acetonitrile/water gradient mixture to give the title compound (153 mg, 68%).

Workup

  1. customThe reaction mixture was quenched with 6N hydrochloric acid
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative HPLC
  7. washeluting with a 5-95% acetonitrile/water gradient mixture

Sources & evidence

ORD record
ord-d591dbd0a0cd461ab48b9583e3930beb
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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