Ethanol → 1-[3-(6-tert-Butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-6-dimethylaminomethyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid amide

HRID 1025647Notes

Reaction equation

HRID 1025647 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[C:18]([CH2:38][OH:39])=[C:19]([N:23]3[C:27]4=[N:28][C:29]([CH2:32][N:33]([CH3:35])[CH3:34])=[CH:30][CH:31]=[C:26]4[C:25]([C:36]#[N:37])=[CH:24]3)[CH:20]=[CH:21][CH:22]=1)[N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].C([OH:42])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[C:18]([CH2:38][OH:39])=[C:19]([N:23]3[C:27]4=[N:28][C:29]([CH2:32][N:33]([CH3:35])[CH3:34])=[CH:30][CH:31]=[C:26]4[C:25]([C:36]([NH2:37])=[O:42])=[CH: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 71008541HCID 71008541, compound

Product 1

HCID 710085841-[3-(6-tert-Butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-6-dimethylaminomethyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid amideYield 30%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

In a 25 mL round-bottomed flask, 1-(3-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-2-(hydroxymethyl)phenyl)-6-((dimethylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (8 mg, 15.3 μmol, Eq: 1.00) and [hydrogen bis(dimethylphosphinito-kP)]platinum (II) (655 μg, 1.53 μmol, Eq: 0.1) were combined with Ethanol (1 mL) and Water (1 mL) to give a colorless solution. The reaction mixture was heated to 45° C. and stirred for 1 h. The crude reaction mixture was concentrated in vacuo. The LCMS of crude shows the desired product. The reaction mixture was diluted with acetonitrile and water and filtered and passed through HPLC purification followed by lyophalization to give 1-[3-(6-tert-Butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-6-dimethylaminomethyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid amide (2.5 mg, 30%, [M+H]+ 543)

Workup

  1. customto give a colorless solution
  2. customThe crude reaction mixture
  3. concentrationwas concentrated in vacuo
  4. additionThe reaction mixture was diluted with acetonitrile and water
  5. filtrationfiltered
  6. custompassed through HPLC purification

Sources & evidence

ORD record
ord-7d843decdf4b45beac14b69788e18351
Source dataset
uspto-grants-2014_05
Patent number
US08729078B2

Reaction notes

Loading…