Sodium hydride → HCID 86641914, compound

HRID 2365585Notes

Reaction equation

HRID 2365585 reaction equation
[H-].[Na+].Cl.[F:4][C:5]([F:24])([F:23])[C:6]([NH:8][C:9]1([CH2:15][NH:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)=[O:7].Br.Br[CH2:27][C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1>CN(C=O)C>[F:19][C:18]([F:21])([F:20])[C:17]([NH:16][CH2:15][C:9]1([NH:8][C:6](=[O:7])[C:5]([F:4])([F:23])[F:24])[CH2:14][CH2:13][N:12]([CH2:27][C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)[CH2:11][CH2:10]1)=[O:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 127522194-(Bromomethyl)pyridine hbrHCID 86641913HCID 86641913, compound

Product 1

HCID 86641914HCID 86641914, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of NaH (170 mg of a 60% dispersion in mineral oil, 4.25 mmol) in anhydrous DMF (20 ml) is added 2,2,2-trifluoro-N-{4-[(2,2,2-trifluoro-acetylamino)-methyl]-piperidin-4-yl}-acetamide hydrochloride) (500 mg, 1.4 mmol) followed by 4-bromomethylpyridine hydrobromide (350 mg, 1.4 mmol). The reaction mixture is stirred at room temperature for 3 hours. The reaction mixture is quenched with sat. NH4Cl solution and is concentrated in vacuo. The residue is purified by column chromatography (basic alumina, MeOH/DCM) to obtain 2,2,2-Trifluoro-N-[1-pyridin-4-ylmethyl-4-(2,2,2-trifluoro-acetylamino)-piperidin-4-ylmethyl]-acetamide as off-white solid; [M+H]+ 413

Workup

  1. customThe reaction mixture is quenched with sat. NH4Cl solution
  2. concentrationis concentrated in vacuo
  3. customThe residue is purified by column chromatography (basic alumina, MeOH/DCM)

Sources & evidence

ORD record
ord-acc1781b59174d4f871b86e4ee3eba59
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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