Tetrahydrofuran → HCID 86673716, compound

HRID 1025601Notes

Reaction equation

HRID 1025601 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]([CH:41]=[O:42])=[C:19]([N:23]3[CH:27]=[C:26]([C:28]#[N:29])[C:25]([NH:30][C:31]4[CH:36]=[CH:35][C:34]([C:37]([OH:40])([CH3:39])[CH3:38])=[CH:33][CH:32]=4)=[N:24]3)[CH:20]=[CH:21][CH:22]=1)[N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].[O:43]1CCCC1>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]([CH:41]=[O:42])=[C:19]([N:23]3[CH:27]=[C:26]([C:28]([NH2:29])=[O:43])[C:25]([NH:30][C:31]4[CH:32]=[CH:33][C:34]([C:37]([OH:40])([CH3:39])[CH3:38])=[CH:35][CH:36]=4)=[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 8028TetrahydrofuranHCID 86673717HCID 86673717, compound

Product 1

HCID 86673716HCID 86673716, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-[3-(6-tert-Butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-2-formyl-phenyl]-3-[4-(1-hydroxy-1-methyl-ethyl)-phenylamino]-1H-pyrazole-4-carbonitrile (78 mg, 0.14 mmol) and dihydrogen tris(dimethylphosphinito)hydroplatinate (7.1 mg, 0.12 eq) were taken up in tetrahydrofuran (3.1 ml) and water (0.31 ml). The material was stirred and heated to reflux (oil bath) for 1 hour. The mixture was cooled to ambient and the volatiles were stripped (rotary evaporator). The crude material was purified by preparative thin layer chromatography (2 plates, eluting first with 7% methanol in methylene chloride and then re-developing with 6% methanol in methylene chloride). The product band was collected, providing desired 1-[3-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-2-formyl-phenyl]-3-[4-(1-hydroxy-1-methyl-ethyl)-phenylamino]-1H-pyrazole-4-carboxylic acid amide as a light yellow powder (41 mg). LC/MS calcd for C32H31FN6O4 (m/e) 582.62, obsd 581.0 (M−H, ES−).

Workup

  1. temperatureheated
  2. temperatureto reflux (oil bath) for 1 hour
  3. temperatureThe mixture was cooled to ambient and the volatiles
  4. custom(rotary evaporator)
  5. customThe crude material was purified by preparative thin layer chromatography (2 plates
  6. washeluting first with 7% methanol in methylene chloride
  7. customThe product band was collected

Sources & evidence

ORD record
ord-80c54ab875184a07a0e4d9a837f6f633
Source dataset
uspto-grants-2014_05
Patent number
US08729078B2

Reaction notes

Loading…