Water → HCID 118023458, compound

HRID 1503353Notes

Reaction equation

HRID 1503353 reaction equation
[CH3:1][C:2]1[C:6]([CH:7]=[O:8])=[CH:5][NH:4][N:3]=1.[H-].[Na+].Cl[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[N:24]([CH3:28])[CH:23]=[C:22]3[C:29](=[O:33])[CH:30]([CH3:32])[CH3:31])[N:13]=1.O>CN(C=O)C>[C:29]([C:22]1[C:21]2[C:25](=[CH:26][CH:27]=[C:19]([NH:18][C:14]3[N:15]=[C:16]([N:4]4[CH:5]=[C:6]([CH:7]=[O:8])[C:2]([CH3:1])=[N:3]4)[CH:17]=[CH:12][N:13]=3)[CH:20]=2)[N:24]([CH3:28])[CH:23]=1)(=[O:33])[CH:30]([CH3:32])[CH3:31]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 118022968HCID 118022968, compoundHCID 1784345503-methyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 118023458HCID 118023458, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-methyl-1H-pyrazole-4-carbaldehyde (273 mg, 2.48 mmol) in anhydrous DMF (5 mL) was added 60% NaH (130 mg, 3.25 mmol) at 0° C. After being stirred for 30 min at room temperature, it was cooled to 0° C. To this, was added intermediate 5 (542 mg, 1.65 mmol) and then stirred for 6 hours at 60° C. Quenching the reaction by addition of ice and 20 mL of water resulted precipitation of brown solids. The resulted solids were collected by filtration, rinsed with water and the dried in vacuo to provide the desired intermediate 6 as a brown solid (424 mg, 80%); MS (ESI) m/z 403 [M+H]+.

Workup

  1. temperatureit was cooled to 0° C
  2. stirringstirred for 6 hours at 60° C
  3. customQuenching
  4. customthe reaction
  5. customresulted
  6. customprecipitation of brown solids
  7. filtrationThe resulted solids were collected by filtration
  8. washrinsed with water
  9. customthe dried in vacuo

Sources & evidence

ORD record
ord-8c4190f744de473dafbe11228a90b83f
Source dataset
uspto-grants-2015_12
Patent number
US09212178B2

Reaction notes

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