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

HRID 1025646Notes

Reaction equation

HRID 1025646 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]([CH2:40][OH:41])=[C:19]([N:23]3[C:27]4=[N:28][C:29]([NH:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])=[CH:30][CH:31]=[C:26]4[C:25]([C:38]#[N:39])=[CH:24]3)[CH:20]=[CH:21][CH:22]=1)[N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].C([OH:44])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]([CH2:40][OH:41])=[C:19]([N:23]3[C:27]4=[N:28][C:29]([NH:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])=[CH:30][CH:31]=[C:26]4[C:25]([C:38]([NH2:39])=[O:44])=[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 710080741-(3-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-2-(hydroxymethyl)phenyl)-6-(2-(dimethylamino)ethylamino)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

Product 1

HCID 710084331-[3-(6-tert-Butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-6-(2-dimethylamino-ethylamino)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid amideYield 71%

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-(2-(dimethylamino)ethylamino)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (19 mg, 34.3 μmol, Eq: 1.00) and [hydrogen bis(dimethylphosphinito-kP)]platinum (II) (1.47 mg, 3.43 μmol, Eq: 0.1) were combined with Ethanol (271 μl) and Water (271 μl) 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, then diluted with acetonitrile and water and filtered. The resultant filtrate was lyophilized to give 1-[3-(6-tert-Butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-6-(2-dimethylamino-ethylamino)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid amide (14.2 mg, 71%, [M+H]+ 572).

Workup

  1. customto give a colorless solution
  2. customThe crude reaction mixture
  3. concentrationwas concentrated in vacuo
  4. additiondiluted with acetonitrile and water
  5. filtrationfiltered

Sources & evidence

ORD record
ord-5f2284eaca07420ca85275f5b391e1a5
Source dataset
uspto-grants-2014_05
Patent number
US08729078B2

Reaction notes

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