Water → HCID 58926847, compound

HRID 1670781Notes

Reaction equation

HRID 1670781 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([NH:10][C:11](=[O:15])OCC)=[N:2]1.[CH2:16]1[CH2:26][CH2:25][N:24]2[C:19](=NC[CH2:22][CH2:23]2)[CH2:18][CH2:17]1.[OH2:27]>CN(C)C=O.CO.Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([NH:10][C:11]([N:24]2[CH2:25][CH2:26][C:16]([C:17]3[CH:18]=[CH:19][CH:3]=[C:4]([CH3:9])[C:5]=3[CH3:6])([OH:27])[CH2:22][CH2:23]2)=[O:15])=[N:2]1

Participants

7

Reactant 3

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 12262771HCID 12262771, compound

Product 1

HCID 58926847HCID 58926847, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Ethyl 1H-indazol-3-ylcarbamate (1.2 g) and the compound (1.46 g) of Starting Material Synthetic Example 106 were dissolved in dimethylformamide (10 ml), DBU (2.3 ml) was added thereto, and the mixture was stirred with heating at 120° C. for 2 hr. After completion of the reaction, the reaction mixture was diluted with methanol (3 ml) and 1N hydrochloric acid and water were added to the mixture. The precipitated solid was collected by filtration and vacuum dried to give 4-(2,3-dimethylphenyl)-4-hydroxy-1-piperidinecarboxylic acid (1H-indazol-3-yl)amide (1.02 g, yield 47%).

Workup

  1. customAfter completion of the reaction
  2. additionwere added to the mixture
  3. filtrationThe precipitated solid was collected by filtration and vacuum
  4. customdried

Sources & evidence

ORD record
ord-8c11d41496b648a18f191b111a091887
Source dataset
uspto-grants-2011_08
Patent number
US07994196B2

Reaction notes

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