Acetic Acid → HCID 58614668, compound

HRID 923120Notes

Reaction equation

HRID 923120 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:23])[C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][C:17]3=[O:22])=[CH:12][CH:11]=2)=[CH:4][C:3]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1.C=O.[C:32](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CC(O)=O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:23])[C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:21][CH2:20][N:19]([CH3:32])[CH2:18][C:17]3=[O:22])=[CH:12][CH:11]=2)=[CH:4][C:3]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 58614637HCID 58614637, compound

Product 1

HCID 58614668HCID 58614668, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

120 mg of N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(2-oxopiperazin-1-yl)benzamide was dissolved in 2 mL of DMF and then treated with 53 mg of paraformaldehyde, 187 mg of sodium triacetoxyborohydride and 0.2 mL of AcOH. After stirring 16 h, the reaction mixture was evaporated and the crude product was purified by reverse phase HPLC to yield N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(4-methyl-2-oxopiperazin-1-yl)benzamide. MS (Q1) 421.3 (M)+.

Workup

  1. customthe reaction mixture was evaporated
  2. customthe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-2e1e15702f7442eba8a3119577442b3b
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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