Acetic Acid → HCID 70494998, compound

HRID 1521778Notes

Reaction equation

HRID 1521778 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]=O)[CH:10]=2)[NH:5][N:4]=1.[C:14](/[CH:16]=[C:17](\[O-:19])/[CH3:18])#[N:15].[Na+].C(O)(=O)C.N1CCCCC1>ClCCl.O>[CH3:1][O:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](/[CH:12]=[C:16](/[C:17](=[O:19])[CH3:18])\[C:14]#[N:15])[CH:10]=2)[NH:5][N:4]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 23687916sodium (1Z)-1-cyanoprop-1-en-2-olateHCID 58407606HCID 58407606, compound

Product 1

HCID 70494998HCID 70494998, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 300 mg (1.704 mmol) 3-methoxy-1H-indazole-5-carbaldehyde (Example 7A), 151 mg (1.442 mmol) sodium (1Z)-1-cyanoprop-1-en-2-olate, 93 μl (1.639 mmol) acetic acid and 11 mg (0.131 mmol) piperidine in dry dichloromethane (10 ml) was refluxed overnight employing a water separator. Upon cooling, a precipitate was formed which was removed by filtration. The filtrate thus obtained was concentrated, and the residue was purified by preparative RP-HPLC (acetonitrile/water gradient) to afford 43 mg (10% of th.) of the title compound.

Workup

  1. temperaturewas refluxed overnight
  2. temperatureUpon cooling
  3. customa precipitate was formed which
  4. customwas removed by filtration
  5. customThe filtrate thus obtained
  6. concentrationwas concentrated
  7. customthe residue was purified by preparative RP-HPLC (acetonitrile/water gradient)

Sources & evidence

ORD record
ord-69bf8cb2d92843abb410d211d82d79f1
Source dataset
uspto-grants-2015_07
Patent number
US09073939B2

Reaction notes

Loading…