Piperazine → HCID 10747297, compound

HRID 2186696Notes

Reaction equation

HRID 2186696 reaction equation
Br[C:2]1[C:3](=[O:48])[N:4]([CH3:47])[C:5](=[O:46])[C:6]=1[C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]=1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]1[NH:29][C:30]2[C:35]([C:36]=1[C:37]1[C:38](=[O:45])[N:39]([CH3:44])[C:40](=[O:43])[C:41]=1Br)=[CH:34][CH:33]=[CH:32][CH:31]=2.CN(C=O)C.[NH:54]1[CH2:59][CH2:58][NH:57][CH2:56][CH2:55]1>CCN(CC)CC>[CH3:47][N:4]1[C:5](=[O:46])[C:6]2[C:7]3[C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[NH:9][C:8]=3[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]3[NH:29][C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][C:35]=4[C:36]=3[C:37]3[C:38](=[O:45])[N:39]([CH3:44])[C:40](=[O:43])[C:41]=3[N:57]3[CH2:58][CH2:59][N:54]([CH2:55][CH2:56]3)[C:2]=2[C:3]1=[O:48]

Participants

5

Reactant 3

HCID 4837PiperazineHCID 6228Dimethylformamide2×HCID 10629024HCID 10629024, compound

Product 1

HCID 10747297HCID 10747297, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent2×

Conditions

Temperature
80 °C

Procedure

0.75 mmol of 3-bromo-4-(2-(12-(3-(4-bromo-1-methyl-2,5-dioxo-2,5-dihydro-1H-3-pyrrolyl)-1H-2-indolyl)dodecyl)-1H-3-indolyl)-1-methyl-2,5-dihydro-1H-pyrrole-2,5-dione is dissolved in 200 ml of absol. DMF, treated with 0.5 ml of abs. NEt3 and heated to 80° C. The solution of 0.75 mmol of piperazine in 100 ml of absol. DMF and 0.5 ml of NEt3 is then slowly added dropwise to the warm solution and the mixture is then stirred at 80° C. for 48 h. The solvent is then removed in vacuo to the greatest possible extent and the residue is treated with 100 ml of 1N HCl. This solution is then extracted with ethyl acetate (in total about 600 ml), the combined extracts are dried over Na2SO4 and the solvent is stripped off in vacuo. Purification is carried out by column chromatography (SiO2, CH2Cl2/EA9.5:0.5) orange crystals, yield: 0.267 g (52%).

Workup

  1. customThe solvent is then removed in vacuo to the greatest possible extent
  2. additionthe residue is treated with 100 ml of 1N HCl
  3. extractionThis solution is then extracted with ethyl acetate (in total about 600 ml)
  4. dry with materialthe combined extracts are dried over Na2SO4
  5. customPurification

Sources & evidence

ORD record
ord-80fb192ee5db44fab9ba878c6f5f1f04
Source dataset
uspto-grants-2002_06
Patent number
US06407102B1

Reaction notes

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