Ethanol → HCID 71008051, compound

HRID 1025654Notes

Reaction equation

HRID 1025654 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:17]1[CH:18]=[C:19]([N:23]3[CH:27]=[C:26]([C:28]#[N:29])[CH:25]=[N:24]3)[CH:20]=[CH:21][CH:22]=1)[N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].C([OH:32])C>O>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:17]1[CH:18]=[C:19]([N:23]3[CH:27]=[C:26]([C:28]([NH2:29])=[O:32])[CH:25]=[N:24]3)[CH:20]=[CH:21][CH:22]=1)[N:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 702EthanolHCID 71008668HCID 71008668, compound

Product 1

HCID 71008051HCID 71008051, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

In a 25 mL round-bottomed flask, 1-(3-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)phenyl)-1H-pyrazole-4-carbonitrile (87 mg, 225 μmol, Eq: 1.00) and hydrido(dimethylyphosphinous acid-kP) (4.82 mg, 11.2 μmol, Eq: 0.05) were combined with Ethanol (1 ml) and Water (1.00 ml) to give a colorless solution. The reaction mixture was heated to 85° C. and stirred for 45 min. After the required reaction time (conversion checked my LCMS and TLC), the reaction was allowed to come to room temperature and the solvent was removed under vacuum. The mixture was then filtered through the HPLC teflon filter and passed through reverphase HPLC and lyophilized overnight to give 1-[3-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-phenyl]-1H-pyrazole-4-carboxylic acid amide (49 mg, 54%, [M+H]+ 406)

Workup

  1. customto give a colorless solution
  2. customAfter the required reaction time (conversion checked my LCMS and TLC)
  3. customto come to room temperature
  4. customthe solvent was removed under vacuum
  5. filtrationThe mixture was then filtered through the HPLC teflon
  6. filtrationfilter
  7. waitlyophilized overnight

Sources & evidence

ORD record
ord-40b9dc32194b451ea337504d1a2d014a
Source dataset
uspto-grants-2014_05
Patent number
US08729078B2

Reaction notes

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