Piperidine → HCID 58073923, compound

HRID 1470668Notes

Reaction equation

HRID 1470668 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([C:14]3[C:19]([F:20])=[C:18]([F:21])[C:17]([C:22]4[CH:27]=[CH:26][C:25]([CH:28]=O)=[CH:24][CH:23]=4)=[C:16]([F:30])[C:15]=3[F:31])[NH:10][C:9]=2[CH:8]=[C:7]([CH3:32])[CH:6]=1)=[O:4].[NH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([C:14]3[C:15]([F:31])=[C:16]([F:30])[C:17]([C:22]4[CH:23]=[CH:24][C:25]([CH2:28][N:33]5[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]5)=[CH:26][CH:27]=4)=[C:18]([F:21])[C:19]=3[F:20])[NH:10][C:9]=2[CH:8]=[C:7]([CH3:32])[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 58073906HCID 58073906, compound

Product 1

HCID 58073923HCID 58073923, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-methyl-2-(2,3,5,6-tetrafluoro-4′-formyl-biphenyl-4-yl)-1H-benzoimidazole-4-carboxylic acid methyl ester (0.13 g, 0.29 mmol) in tetrahydrofuran (100 mL) was added piperidine (0.03 g, 0.35 mmol). The reaction mixture was stirred at room temperature for 30 minutes. Sodium triacetoxyborohydride (0.374 g, 1.76 mmol) was added and stirring continued for another 1 hour. The progression of the reaction was monitored by TLC. The reaction mixture quenched with sodium bicarbonate solution (3 mL) and concentrated. The residue was then extracted with ethyl acetate and the combined organic layered were washed with water and brine, dried over anhydrous sodium sulphate and concentrated to get the title compound (0.145 g, 96.66%) which was directly taken to next step.

Workup

  1. stirringstirring
  2. waitcontinued for another 1 hour
  3. customThe reaction mixture quenched with sodium bicarbonate solution (3 mL)
  4. concentrationconcentrated
  5. extractionThe residue was then extracted with ethyl acetate
  6. washthe combined organic layered were washed with water and brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-70c28d36f47641ec8d54b728be292a75
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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