1,1'-Carbonyldiimidazole → HCID 178481556, compound

HRID 538066Notes

Reaction equation

HRID 538066 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:13][N:14]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[C:18](=[O:25])[N:17]([CH2:26][C@H:27]2[CH2:32][CH2:31][C@H:30]([C:33](O)=[O:34])[CH2:29][CH2:28]2)[CH2:16][C:15]1=[O:36].[N:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[N:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1>C(Cl)Cl>[CH3:13][N:14]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[C:18](=[O:25])[N:17]([CH2:26][C@H:27]2[CH2:28][CH2:29][C@H:30]([C:33]([N:46]3[CH2:47][CH2:48][N:43]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][N:37]=4)[CH2:44][CH2:45]3)=[O:34])[CH2:31][CH2:32]2)[CH2:16][C:15]1=[O:36]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 944591-(2-Pyridyl)piperazineHCID 178481557HCID 178481557, compound

Product 1

HCID 178481556HCID 178481556, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Solid CDI (0.18 mmol, 0.03 g) was added to a solution of trans-4-(1-Methyl-2,5-dioxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-ylmethyl)-cyclo hexanecarboxylic 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 (0.22 mmol, 32 μL) was added and the reaction mixture was left stirring at room temperature under argon overnight. 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 42 mg (yield 59%) of the titled compound

Workup

  1. waitthe reaction mixture was left
  2. customThe solvent was removed under reduced pressure
  3. customthe crude purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-696da41762014a0fbade8d036be764e3
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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