Methanol → HCID 58012397, compound

HRID 1698546Notes

Reaction equation

HRID 1698546 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH:9][C:10]2[N:14]([CH3:15])[C:13]3[C:16]([C:20]4[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=4[CH:22]=O)=[CH:17][CH:18]=[CH:19][C:12]=3[N:11]=2)=[C:4]([O:28][CH3:29])[CH:3]=1.CO.[CH3:32][NH2:33].[BH4-].[Na+]>O.C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH:9][C:10]2[N:14]([CH3:15])[C:13]3[C:16]([C:20]4[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=4[CH2:22][NH:33][CH3:32])=[CH:17][CH:18]=[CH:19][C:12]=3[N:11]=2)=[C:4]([O:28][CH3:29])[CH:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 6329MethylamineHCID 4311764Sodium borohydride2×HCID 58012434HCID 58012434, compound

Product 1

HCID 58012397HCID 58012397, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 33 mg (0.0813 mmol) of 2-[2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazol-7-yl]benzaldehyde, 0.033 mL (0.325 mmol) of 40% methanol solution of methyl amine and 1 mL of ethanol was refluxed for 4 hours. After cooling, 9.2 mg (0.244 mmol) of sodium borohydride was added. The mixture was stirred at room temperature for 4 hours, and 15 mg (0.407 mmol) of sodium borohydride was added. After stirring at room temperature for 15 hours, the reaction mixture was diluted with water and extracted with ethyl acetate (X2). The combined organic layer was washed with brine (X1), dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative HPLC and basic silica gel column chromatography eluting with a 50-100% ethylacetate/n-hexane gradient mixture to give 5 mg (17%) of the title compound.

Workup

  1. temperaturewas refluxed for 4 hours
  2. temperatureAfter cooling
  3. stirringAfter stirring at room temperature for 15 hours
  4. extractionextracted with ethyl acetate (X2)
  5. washThe combined organic layer was washed with brine (X1)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by preparative HPLC and basic silica gel column chromatography
  9. washeluting with a 50-100% ethylacetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-20dcc961e67647a88bdb48e9c1eb3707
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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