(S)-2-Benzylpiperazine → HCID 20816900, compound

HRID 897416Notes

Reaction equation

HRID 897416 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[C:12]2[N:13]([CH:25]=[N:26][N:27]=2)[C:14](SC)=[N:15][C:16]=1[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.[CH2:28]([C@H:35]1[CH2:40][NH:39][CH2:38][CH2:37][NH:36]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C=O)C>[CH2:28]([C@@H:35]1[NH:36][CH2:37][CH2:38][N:39]([C:14]2[N:13]3[CH:25]=[N:26][N:27]=[C:12]3[C:11]([C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)=[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[N:15]=2)[CH2:40]1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 20760001(S)-2-BenzylpiperazineHCID 22346600HCID 22346600, compound

Product 1

HCID 20816900HCID 20816900, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

8-(2-naphthyl)-5-methylthio-7-(4-pyridyl)-1,2,4-triazolo[4,3-c]pyrimidine (200 mg, 0.54 mmol), K3CO3 (100 mg) and (S)-2-benzylpiperazine (170 mg, 0.97 mmol) were combined in dry DMF (ca. 4 mL) and the mixture was heated at 100° C. for 48 h. The reaction was cooled to RT, and partitioned between water and ethyl acetate. The organic layer was dried over Na2SO4 and then concentrated in vacuo. The residue was purified by flash chromatography (2-8% MeOH/NH3:CH2Cl2) to provide the product as a tan solid; MS (m/z) 498.3 (M+H)+; C31H27N7 requir. 497.59.

Workup

  1. temperatureThe reaction was cooled to RT
  2. custompartitioned between water and ethyl acetate
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (2-8% MeOH/NH3:CH2Cl2)

Sources & evidence

ORD record
ord-6c46afab90814b499da3d651e4445c6c
Source dataset
uspto-grants-2005_07
Patent number
US06921762B2

Reaction notes

Loading…