1-(2-Hydroxyethyl)piperazine → HCID 135413559, compound

HRID 2217127Notes

Reaction equation

HRID 2217127 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[NH2:13][CH2:14][C:15]1[CH:37]=[CH:36][C:18]([C:19]([N:21]2[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[NH:25][C:24]3[N:32]([CH3:35])[N:33]=[CH:34][C:23]=3[CH2:22]2)=[O:20])=[CH:17][C:16]=1[CH3:38].[OH:39][CH2:40][CH2:41][N:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1>CN(C=O)C>[OH:39][CH2:40][CH2:41][N:42]1[CH2:47][CH2:46][N:45]([C:1]([NH:13][CH2:14][C:15]2[CH:37]=[CH:36][C:18]([C:19]([N:21]3[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=4[NH:25][C:24]4[N:32]([CH3:35])[N:33]=[CH:34][C:23]=4[CH2:22]3)=[O:20])=[CH:17][C:16]=2[CH3:38])=[O:2])[CH2:44][CH2:43]1

Participants

5

Reactant 3

HCID 76771-(2-Hydroxyethyl)piperazineHCID 682631,1'-CarbonyldiimidazoleHCID 135829584HCID 135829584, compound

Product 1

HCID 135413559HCID 135413559, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1,1′-Carbonyldiimidazole (20 mg, 0.19 mmol) was added to a solution of 5-(4-(aminomethyl)-3-methylbenzoyl)-1-methyl-4,10-dihydropyrazolo-[5,4-b][1,5]benzodiazepine (31 mg, 0.09 mmol) in DMF (3 ml). The solution was stirred at room temperature for 1 h, a solution of 1-(2-hydroxyethyl)-piperazine (13 mg, 0.10 mmol) in DMF (2 ml) was added and stirring was continued for 72 h. The solution was concentrated in vacuo and the residue was partitioned between chloroform and brine. The organic layer was separated and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant 7% methanol/chloroform) to give a white solid identified as 5-(4-(4-(2-hydroxyethyl)piperazine-1-carbonylaminomethyl)-3-methylbenzoyl)-1-methyl-4,10-dihydropyrazolo[5,4-b][1,5](22 mg, 48%).

Workup

  1. stirringstirring
  2. waitwas continued for 72 h
  3. concentrationThe solution was concentrated in vacuo
  4. customthe residue was partitioned between chloroform and brine
  5. customThe organic layer was separated
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel (eluant 7% methanol/chloroform)
  8. customto give a white solid

Sources & evidence

ORD record
ord-282b3df9de6a4979bb9f3050335d8543
Source dataset
uspto-grants-2008_08
Patent number
US07407949B2

Reaction notes

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