Lithium Hydroxide → 2-[(3,5-dimethoxyphenyl)amino]-1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-1H-benzimidazole-5-carboxylic acid

HRID 1727416Notes

Reaction equation

HRID 1727416 reaction equation
[OH-].[Li+].C[O:4][C:5]([C:7]1[CH:39]=[CH:38][C:10]2[N:11]([CH2:25][CH2:26][CH2:27][N:28]([CH3:37])[CH2:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=3)[C:12]([NH:14][C:15]3[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[CH:16]=3)=[N:13][C:9]=2[CH:8]=1)=[O:6]>O1CCCC1.O>[CH3:22][O:21][C:19]1[CH:20]=[C:15]([NH:14][C:12]2[N:11]([CH2:25][CH2:26][CH2:27][N:28]([CH3:37])[CH2:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=3)[C:10]3[CH:38]=[CH:39][C:7]([C:5]([OH:6])=[O:4])=[CH:8][C:9]=3[N:13]=2)[CH:16]=[C:17]([O:23][CH3:24])[CH:18]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69027642methyl-2-[(3,5-dimethoxyphenyl)amino]-1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-1H-benzimidazole-5-carboxylate

Product 1

HCID 690297442-[(3,5-dimethoxyphenyl)amino]-1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-1H-benzimidazole-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

Lithium hydroxide (0.350 g, 4 eq) is added to a solution of methyl-2-[(3,5-dimethoxyphenyl)amino]-1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-1H-benzimidazole-5-carboxylate (1.05 g, 1 eq) in a mixture of tetrahydrofuran (10 ml) and water (5 ml). The mixture is stirred at 65° C. for 18 hours then cooled down to ambient temperature and concentrated under reduced pressure at 40° C. Ethyl acetate and water are added to the residue. The mixture is acidified by adding acetic acid to pH 5. After decanting and extracting, the combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. Purification by flash chromatography on silica gel (eluent: dichloromethane/ethanol 95/5 to 70/30) produces the expected compound in the form of a white foam (0.93 g, 91% yield).

Workup

  1. temperaturethen cooled down to ambient temperature
  2. concentrationconcentrated under reduced pressure at 40° C
  3. additionEthyl acetate and water are added to the residue
  4. additionby adding acetic acid to pH 5
  5. customAfter decanting
  6. extractionextracting
  7. dry with materialthe combined organic phases are dried over sodium sulphate
  8. concentrationconcentrated under reduced pressure
  9. customPurification by flash chromatography on silica gel (eluent: dichloromethane/ethanol 95/5 to 70/30)

Sources & evidence

ORD record
ord-f32812812bae42ea99ef081b13b1466a
Source dataset
uspto-grants-2009_02
Patent number
US07495110B2

Reaction notes

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