Tetrahydrofuran → Formate

HRID 1507167Notes

Reaction equation

HRID 1507167 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[F:8][C:9]1[CH:10]=[C:11]([C:16]2[CH:17]=[CH:18][C:19](=[O:38])[N:20]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]4[N:33]=[C:32]([C:34](Cl)(Cl)Cl)[O:31][N:30]=4)[CH:24]=3)[N:21]=2)[CH:12]=[C:13]([F:15])[CH:14]=1.C1[CH2:43][O:42]CC1>>[F:8][C:9]1[CH:10]=[C:11]([C:16]2[CH:17]=[CH:18][C:19](=[O:38])[N:20]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]4[N:33]=[C:32]([N:5]5[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]5)[O:31][N:30]=4)[CH:24]=3)[N:21]=2)[CH:12]=[C:13]([F:15])[CH:14]=1.[F:8][C:9]1[CH:10]=[C:11]([C:16]2[CH:17]=[CH:18][C:19](=[O:38])[N:20]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]4[N:33]=[C:32]([C:34]([N:5]5[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]5)=[O:42])[O:31][N:30]=4)[CH:24]=3)[N:21]=2)[CH:12]=[C:13]([F:15])[CH:14]=1.[CH:43]([O-:42])=[O:31]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 531671-MethylpiperazineHCID 59534498HCID 59534498, compound

Product 3

HCID 283FormateHCID 24830286HCID 24830286, compoundHCID 24830918HCID 24830918, compound

Procedure

100 mg (1.00 mmol) of 1-methylpiperazine are added to a solution of 242 mg (0.50 mmol) of 6-(3,5-difluorophenyl)-2-[3-(5-trichloromethyl-1,2,4-oxadiazol-3-yl)benzyl]-2H-pyridazin-3-one in 1 ml of THF, and the mixture is stirred at room temperature for 18 hours. The reaction mixture is evaporated and separated by preparative HPLC, giving 6-(3,5-difluorophenyl)-2-{3-[5-(4-methylpiperazin-1-yl)-1,2,4-oxadiazol-3-yl]benzyl}-2H-pyridazin-3-one (“A20”) formate as colourless oil (ESI 465) and 6-(3,5-difluorophenyl)-2-{3-[5-(4-methylpiperazine-1-carbonyl)-1,2,4-oxadiazol-3-yl]benzyl}-2H-pyridazin-3-one (“A21”) formate as colourless solid (ESI 493);

Workup

  1. customThe reaction mixture is evaporated
  2. customseparated by preparative HPLC

Sources & evidence

ORD record
ord-8c61635369c740b69634fb6c0e79e284
Source dataset
uspto-grants-2015_12
Patent number
US09221806B2

Reaction notes

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