4-Cyclopropylmethoxy-3-methoxy-2-chloromethyl pyridine hydrochloride → 5-Carbomethoxy-6-methyl-2-[[(4-cyclopropylmethoxy-3-methoxy-2-pyridinyl)methyl]thio]-1H-benzimidazole

HRID 1647156Notes

Reaction equation

HRID 1647156 reaction equation
[C:1]([C:5]1[C:14]([CH3:15])=[CH:13][C:8]2[NH:9][C:10]([SH:12])=[N:11][C:7]=2[CH:6]=1)([O:3][CH3:4])=[O:2].Cl.[CH:17]1([CH2:20][O:21][C:22]2[CH:27]=[CH:26][N:25]=[C:24]([CH2:28]Cl)[C:23]=2[O:30][CH3:31])[CH2:19][CH2:18]1>CO>[C:1]([C:5]1[C:14]([CH3:15])=[CH:13][C:8]2[NH:9][C:10]([S:12][CH2:28][C:24]3[C:23]([O:30][CH3:31])=[C:22]([O:21][CH2:20][CH:17]4[CH2:19][CH2:18]4)[CH:27]=[CH:26][N:25]=3)=[N:11][C:7]=2[CH:6]=1)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 2

HCID 199264764-Cyclopropylmethoxy-3-methoxy-2-chloromethyl pyridine hydrochlorideHCID 178497010HCID 178497010, compound

Product 1

HCID 199264705-Carbomethoxy-6-methyl-2-[[(4-cyclopropylmethoxy-3-methoxy-2-pyridinyl)methyl]thio]-1H-benzimidazoleYield 100.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 5-carbomethoxy-6-methyl-2-mercapto-1H-benzimidazole (0.58 g, 2.6 mmol) in methanol (25 ml) aqueous NaOH (1.0 ml 5M, 5.0 mmol) and 4-cyclopropylmethoxy-3-methoxy-2-chloromethyl pyridine hydrochloride (prepared according to processes known per se.) (0.63 g, 2.4 mmol) dissolved in methanol (25 ml were added in the given order. The mixture was refluxed for one hour whereupon the solution was evaporated. The residue was partitioned between methylene chloride and water. After separation the organic solution was dried over Na2SO4 and evaporated giving a yellow syrup (1.0 g, 100%).

Workup

  1. additionwere added in the given order
  2. temperatureThe mixture was refluxed for one hour whereupon the solution
  3. customwas evaporated
  4. customThe residue was partitioned between methylene chloride and water
  5. customAfter separation the organic solution
  6. dry with materialwas dried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-340f439e204b4d43b5533e3fc06000dc
Source dataset
uspto-grants-1995_07
Patent number
US05430042

Reaction notes

Loading…