Hydrochloric Acid → HCID 58614658, compound

HRID 922996Notes

Reaction equation

HRID 922996 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:25])[C:11]2[CH:16]=[CH:15][C:14]([CH2:17][N:18]3[CH2:23][CH2:22][NH:21][CH2:20][C:19]3=[O:24])=[CH:13][CH:12]=2)=[CH:5][C:4]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1.C=O.[C:34](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CC(O)=O.CN(C=O)C>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:25])[C:11]2[CH:12]=[CH:13][C:14]([CH2:17][N:18]3[CH2:23][CH2:22][N:21]([CH3:34])[CH2:20][C:19]3=[O:24])=[CH:15][CH:16]=2)=[CH:5][C:4]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 58614766HCID 58614766, compound

Product 1

HCID 58614658HCID 58614658, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

To 200 mg of the HCl salt of N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-((2-oxopiperazin-1-yl)methyl)benzamide was added 55 mg of Paraformaldehyde and 185 mg of Sodium Triacetoxyborohydride in 1 mL of 2% AcOH in DMF. After completion, the reaction is extracted once with bicarbonate and brine in Ethyl Acetate, dried over Magnesium Sulfate, concentrated and purified by reverse phase HPLC to give pure N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-((4-methyl-2-oxopiperazin-1-yl)methyl)benzamide. MS (Q1) 435.3 (M)+.

Workup

  1. extractionAfter completion, the reaction is extracted once with bicarbonate and brine in Ethyl Acetate
  2. dry with materialdried over Magnesium Sulfate
  3. concentrationconcentrated
  4. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-6eedfc7d19284df8a00553dfadded0fc
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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