1-Methylpiperazine → (2-Chloro-9-cyclopentyl-purin-6-yl)-{2-[3-(4-methyl-piperazin-1-yl)-propoxy]-phenyl}-amine

HRID 1162987Notes

Reaction equation

HRID 1162987 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][C:13]1[N:21]=[C:20]([Cl:22])[N:19]=[C:18]2[C:14]=1[N:15]=[CH:16][N:17]2[CH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1.[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>O>[Cl:22][C:20]1[N:19]=[C:18]2[C:14]([N:15]=[CH:16][N:17]2[CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[C:13]([NH:12][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][CH2:4][CH2:3][CH2:2][N:32]2[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][CH2:31]2)[N:21]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 11774121HCID 11774121, compound

Product 1

HCID 11784673(2-Chloro-9-cyclopentyl-purin-6-yl)-{2-[3-(4-methyl-piperazin-1-yl)-propoxy]-phenyl}-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

[2-(3-Chloro-propoxy)-phenyl]-(2-chloro-9-cyclopentyl-purin-6-yl)-amine (0.4 mmol) are stirred at RT in N-methylpiperazine (0.3 ml) for 12 hours. The mixture is diluted with water and extracted 3 times with ethyl acetate. The combined organic phases are washed with brine and the extract is dried over sodium sulfate and evaporated. The residue is purified by flash chromatography on silica gel with (CH2Cl2/MeOH=9:1) as mobile phase. The product containing fractions are combined and evaporated. A pale oil with Rf=0.25 (CH2Cl2/MeOH=9:2) is obtained.

Workup

  1. extractionextracted 3 times with ethyl acetate
  2. washThe combined organic phases are washed with brine
  3. dry with materialthe extract is dried over sodium sulfate
  4. customevaporated
  5. customThe residue is purified by flash chromatography on silica gel with (CH2Cl2/MeOH=9:1) as mobile phase
  6. additionThe product containing fractions
  7. customevaporated
  8. customA pale oil with Rf=0.25 (CH2Cl2/MeOH=9:2) is obtained

Sources & evidence

ORD record
ord-d4907f8e37b64bde982dcda49624192a
Source dataset
uspto-grants-2010_10
Patent number
US07820818B2

Reaction notes

Loading…