Methylamine → HCID 21876112, compound

HRID 1454741Notes

Reaction equation

HRID 1454741 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:18]3[CH:19]=[C:20]([Cl:26])[C:21]([C:23]([NH2:25])=[O:24])=[CH:22][C:17]=3[N:16]=[C:15]2[CH2:27][CH3:28])=[CH:10][CH:9]=1)(=O)=O.[CH3:29][NH2:30]>O>[Cl:26][C:20]1[C:21]([C:23]([NH2:25])=[O:24])=[CH:22][C:17]2[N:16]=[C:15]([CH2:27][CH3:28])[N:14]([C:11]3[CH:10]=[CH:9][C:8]([CH2:7][CH2:6][NH:30][CH3:29])=[CH:13][CH:12]=3)[C:18]=2[CH:19]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 21876263HCID 21876263, compound

Product 1

HCID 21876112HCID 21876112, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-{4-[5-(aminocarbonyl)-6-chloro-2-ethyl-1H-benzimidazol-1-yl]phenyl}ethyl methanesulfonate (step 1, 304 mg, 0.72 mmol), a solution of methyl amine (40% in methanol, 10 ml) and water (5 ml) in a sealed tube was heated overnight at 100° C. The reaction mixture was partitioned between dichloromethane (30 ml) and water (30 ml). The organic phase was separated and the aqueous phase was extracted with dichloromethane (50 ml). The combined organic phases were washed with brine (50 ml) and dried (Na2SO4). After removal of solvent, the crude product was purified by TLC with dichloromethane/methanol (10: 1) to afford 154 mg (60%) of the title compound as yellow solids.

Workup

  1. customThe reaction mixture was partitioned between dichloromethane (30 ml) and water (30 ml)
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted with dichloromethane (50 ml)
  4. washThe combined organic phases were washed with brine (50 ml)
  5. dry with materialdried (Na2SO4)
  6. customAfter removal of solvent
  7. customthe crude product was purified by TLC with dichloromethane/methanol (10: 1)

Sources & evidence

ORD record
ord-13dded2f7285411889ec16cf5aa74d2c
Source dataset
uspto-grants-2009_01
Patent number
US07479564B2

Reaction notes

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