6-fluoro-4H-1,3-benzodioxine-8-carbaldehyde → HCID 178510304, compound

HRID 2202622Notes

Reaction equation

HRID 2202622 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=2)[C:3]=1[C:15]#[N:16].[F:17][C:18]1[CH:27]=[C:26]([CH:28]=O)[C:21]2[O:22][CH2:23][O:24][CH2:25][C:20]=2[CH:19]=1>CCO.N1CCCCC1>[Cl:14][C:10]1[CH:9]=[C:8]([NH:7][C:4]2[C:3]([C:15]#[N:16])=[C:2]([N:1]=[CH:28][C:26]3[C:21]4[O:22][CH2:23][O:24][CH2:25][C:20]=4[CH:19]=[C:18]([F:17])[CH:27]=3)[NH:6][N:5]=2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 27799056-fluoro-4H-1,3-benzodioxine-8-carbaldehydeHCID 106811675-Amino-3-(3-chloro-phenylamino)-4-cyano-pyrazole

Product 1

HCID 178510304HCID 178510304, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

5-amino-3-((3-chlorophenyl)amino)-1H-pyrazole-4-carbonitrile (100 mg) was then suspended in EtOH (4 mL) and 6-fluoro-4H-1,3-benzodioxine-8-carbaldehyde (1 eq.) and piperidine (1 drop) were added. Stirred at reflux until intermediate was absent (HPLC). After reaction was complete (18 hrs) it was brought to room temperature and filtered to obtain A29 as a yellow powder. Powder was washed with EtOH. Product was allowed to dry under vacuum for 1 hr (103 mg, 60% yield).

Workup

  1. temperatureat reflux until intermediate
  2. customAfter reaction
  3. custom(18 hrs) it
  4. customwas brought to room temperature
  5. filtrationfiltered
  6. customto obtain A29 as a yellow powder
  7. washPowder was washed with EtOH
  8. customto dry under vacuum for 1 hr (103 mg, 60% yield)

Sources & evidence

ORD record
ord-23ed46cd2d474682a96647c674a8924a
Source dataset
uspto-grants-2016_06
Patent number
US09365556B2

Reaction notes

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