Stannous chloride dihydrate → Methyl 2-[4-{5-amino-2-(4-chlorophenyl)benzyloxy}-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylate

HRID 1835587Notes

Reaction equation

HRID 1835587 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:41]=[CH:40][C:39]([N+:42]([O-])=O)=[CH:38][C:9]=2[CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:22]([CH:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)[C:21]4[CH:29]=[CH:30][C:31]([C:33]([O:35][CH3:36])=[O:34])=[CH:32][C:20]=4[N:19]=3)=[C:14]([F:37])[CH:13]=2)=[CH:4][CH:3]=1.O.O.[Sn](Cl)Cl>C(O)C>[NH2:42][C:39]1[CH:40]=[CH:41][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[C:9]([CH:38]=1)[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:22]([CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[C:21]3[CH:29]=[CH:30][C:31]([C:33]([O:35][CH3:36])=[O:34])=[CH:32][C:20]=3[N:19]=2)=[C:14]([F:37])[CH:13]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 21943015HCID 21943015, compound

Product 1

HCID 21943052Methyl 2-[4-{5-amino-2-(4-chlorophenyl)benzyloxy}-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylateYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 2-[4-{2-(4-chlorophenyl)-5-nitrobenzyloxy}-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylate (1.9 g) obtained in Example 337 was suspended in ethanol (40 ml), and tin(II) chloride dihydrate (3.5 g) was added, which was followed by refluxing under heating for 30 min. The reaction mixture was concentrated under reduced pressure, 4N sodium hydroxide was added and the mixture was extracted with chloroform. The organic layer was washed with 2N sodium hydroxide and water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Diisopropyl ether was added to the residue, and the precipitated crystals were collected by filtration to give the title compound (1.5 g, yield 82%).

Workup

  1. temperatureby refluxing
  2. temperatureunder heating for 30 min
  3. concentrationThe reaction mixture was concentrated under reduced pressure, 4N sodium hydroxide
  4. additionwas added
  5. extractionthe mixture was extracted with chloroform
  6. washThe organic layer was washed with 2N sodium hydroxide and water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. additionDiisopropyl ether was added to the residue
  10. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-6b9458eede4642f0a30e2f755b2fd8f7
Source dataset
uspto-grants-2004_08
Patent number
US06770666B2

Reaction notes

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