1-Methylpiperazine → HCID 66886087, compound

HRID 1519063Notes

Reaction equation

HRID 1519063 reaction equation
Cl.[Cl:2][CH:3]([C:8]1[C:9](=[O:17])[C:10]([OH:16])=[C:11]([CH3:15])[N:12]([CH3:14])[CH:13]=1)[C:4]([F:7])([F:6])[F:5].[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>CO>[ClH:2].[OH:16][C:10]1[C:9](=[O:17])[C:8]([CH:3]([N:22]2[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]2)[C:4]([F:7])([F:6])[F:5])=[CH:13][N:12]([CH3:14])[C:11]=1[CH3:15]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 86672815HCID 86672815, compound

Product 1

HCID 66886087HCID 66886087, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Hydroxy-1,2-dimethyl-5-[2,2,2-trifluoro-1-(4-methylpiperazin-1-yl)ethyl]pyridin-4(1H)-one hydrochloride (Apo7063) was prepared from 5-(1-chloro-2,2,2-trifluoroethyl)-3-hydroxy-1,2-dimethylpyridin-4(1H)-one hydrochloride (550 mg, 1.9 mmol) and 1-methylpiperazine (3.0 mL, 27.0 mmol) was added. The reaction was stopped when analysis of the HPLC chromatogram (Method 1) of the reaction mixture complete conversion. The reaction mixture was concentrated to give a solid. To the solid was added methanol (2 mL), the mixture was vortexed and filtered. Thus, Apo7063 was obtained as a solid (280 mg). Yield=41%; HPLC Method 1, purity (AUC)=99.8% at 280 nm; 1H NMR (DMSO-D6+a few drops of D2O) δ (ppm): 7.69 (s, 1H), 4.93 (q, J=9.7 Hz, 1H), 3.70 (s, 3H), 2.60-3.40 (b, 8H), 2.69 (s, 3H), 2.29 (s, 3H); MS-ESI m/z 320 [M+1]+ (100%), 220.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated
  3. customto give a solid
  4. filtrationfiltered

Sources & evidence

ORD record
ord-86b563fd79d94f34b3d54511d1e35abd
Source dataset
uspto-grants-2015_07
Patent number
US09073865B2

Reaction notes

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