Tetrahydrofuran → HCID 71008571, compound

HRID 1025605Notes

Reaction equation

HRID 1025605 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[CH:27]=[C:26]([C:28]#[N:29])[C:25]([NH:30][C:31]4[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][N:32]=4)=[N:24]3)[CH:20]=[CH:21][CH:22]=1)[N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].[O:40]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]([CH2:38][OH:39])=[C:19]([N:23]3[CH:27]=[C:26]([C:28]([NH2:29])=[O:40])[C:25]([NH:30][C:31]4[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][N:32]=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 71008562HCID 71008562, compound

Product 1

HCID 71008571HCID 71008571, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-[3-(6-tert-Butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-3-(5-chloro-pyridin-2-ylamino)-1H-pyrazole-4-carbonitrile (111 mg, 0.204 mmol) and dihydrogen tris(dimethylphosphinito)hydroplatinate (10.5 mg, 0.025 mmol) were taken up in tetrahydrofuran (3.8 ml) and water (0.38 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 remainder was purified by preparative thin layer chromatography (2 plates, eluting first with 7% methanol in methylene chloride and then re-developing again with 7% methanol in methylene chloride). The product band was collected, providing the desired 1-[3-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-3-(5-chloro-pyridin-2-ylamino)-1H-pyrazole-4-carboxylic acid amide as an off-white powder (70 mg). LC/MS calc'd for C28H25ClFN7O3 (m/e) 561.99, obs'd 562 (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 remainder 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-d2609d2f7ed942199ae50e69b02a1db2
Source dataset
uspto-grants-2014_05
Patent number
US08729078B2

Reaction notes

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