1,1'-Carbonyldiimidazole → HCID 178516770, compound

HRID 538064Notes

Reaction equation

HRID 538064 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[O:13]=[C:14]1[NH:20][C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[C:17](=[O:25])[N:16]([CH2:26][C@H:27]2[CH2:32][CH2:31][C@H:30]([C:33](O)=[O:34])[CH2:29][CH2:28]2)[CH2:15]1.[N:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[N:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1>C(Cl)Cl>[N:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[N:42]1[CH2:43][CH2:44][N:45]([C:33]([C@H:30]2[CH2:29][CH2:28][C@H:27]([CH2:26][N:16]3[C:17](=[O:25])[C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[NH:20][C:14](=[O:13])[CH2:15]3)[CH2:32][CH2:31]2)=[O:34])[CH2:46][CH2:47]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 944591-(2-Pyridyl)piperazineHCID 178516771HCID 178516771, compound

Product 1

HCID 178516770HCID 178516770, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

CDI (0.18 mmol, 0.03 g) was added to a solution of trans-4-(2,5-Dioxo-1,2,3,5 tetrahydrobenzo[e][1,4]diazepin-4-ylmethyl)-cyclohexanecarboxylic acid (0.16 mmol, 0.05 g) in dry DCM (1 mL) under argon. After 1 h at room temperature, 1-Pyridin-2-yl-piperazine (0.24 mmol, 35 μL) was added and the reaction mixture was left stirring at room temperature under argon overnight. The DCM solution was washed with water, the solvent was removed under reduced pressure and the crude purified by column chromatography on silica gel using DCM/MeOH 95/5 as eluent to give 45 mg (yield 59%) of the titled compound.

Workup

  1. waitthe reaction mixture was left
  2. washThe DCM solution was washed with water
  3. customthe solvent was removed under reduced pressure
  4. customthe crude purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c4a6b59ddaae479b9308e2ec8b1e6190
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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