1,1'-Carbonyldiimidazole → HCID 178517124, compound

HRID 538078Notes

Reaction equation

HRID 538078 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[CH2:5][CH2:4][N:3]1[CH2:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([C:20]([OH:22])=O)[CH2:16][CH2:15]1.C1N=CN(C(N2C=NC=C2)=O)C=1.[N:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1>C(Cl)Cl>[N:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[N:41]1[CH2:42][CH2:43][N:44]([C:20]([C@H:17]2[CH2:18][CH2:19][C@H:14]([CH2:13][N:3]3[CH2:4][CH2:5][C:6]4[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=4[NH:8][C:2]3=[O:1])[CH2:15][CH2:16]2)=[O:22])[CH2:45][CH2:46]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 944591-(2-Pyridyl)piperazineHCID 178517125HCID 178517125, compound

Product 1

HCID 178517124HCID 178517124, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of trans-4-(2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-ylmethyl)-cyclohexanecarboxylic acid (52 mg, 0.17 mmol) in dry DCM (2 mL) was added CDI (50 mg, 0.31 mmol). The resulting mixture was stirred at room temperature for 2 h, then 1-Pyridin-2-yl-piperazine (44 μL, 0.56 mmol) was added. The reaction mixture was stirred at room temperature for 1.5 h. Then solvent was removed under reduced pressure and crude was purified by crystallization from acetonitrile.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1.5 h
  2. customThen solvent was removed under reduced pressure and crude
  3. customwas purified by crystallization from acetonitrile

Sources & evidence

ORD record
ord-ccb9293795e54424a454c44d748c9606
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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