1,1'-Carbonyldiimidazole → HCID 10568741, compound
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=O)=[N:2]1.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:25][CH:26]1[CH2:31][CH2:30][N:29]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:28][CH2:27]1>CN(C=O)C>[CH2:32]([N:29]1[CH2:30][CH2:31][CH:26]([NH:25][C:10]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][N:2]=2)=[O:12])[CH2:27][CH2:28]1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A stirred solution of 1-H-indazole-3-carboxylic acid (8.11 g, 50.0 mmol) in dry DMF (140 ml) under argon atmosphere was added CDI (8.92 g, 55 mmol) and heated at 60° C. for 2 h. The mixture was cooled to room temperature, dropwise added 4-amino-1-benzylpiperidine (9.51 g, 50.0 mmol) previously dissolved in DMF (20 ml). The mixture was heated at 60° C. for 2 h, cooled to room temperature and the solvent evaporated in vacuo. The residue was added CH2Cl2 (250 ml) and the organic layer washed with H2O (100 ml), 1 N aqueous NaOH (100 ml), H2O (100 ml) and brine (100 ml). The organic layer was dried over Na2SO4, filtered and evaporated in vacuo. The residue was recrystalilized from EtOH to leave the expected product as a white solid (14.23 g, 85.1%).
Workup
- temperatureThe mixture was cooled to room temperature
- temperatureThe mixture was heated at 60° C. for 2 h
- temperaturecooled to room temperature
- customthe solvent evaporated in vacuo
- additionThe residue was added CH2Cl2 (250 ml)
- washthe organic layer washed with H2O (100 ml), 1 N aqueous NaOH (100 ml), H2O (100 ml) and brine (100 ml)
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-ef4c28dda8374351bd56ab1bfceac9d6
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07834010B2
Reaction notes
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