2-Benzo-1,2,5-thiadiazol-5-ylmethyl-6-(3,4,5-trifluorophenyl)-2H-pyridazin-3-one → 2-(3,4-Diaminobenzyl)-6-(3,4,5-trifluorophenyl)-2H-pyridazin-3-one

HRID 2093351Notes

Reaction equation

HRID 2093351 reaction equation
[N:1]1S[N:4]=[C:3]2[CH:6]=[C:7]([CH2:10][N:11]3[C:16](=[O:17])[CH:15]=[CH:14][C:13]([C:18]4[CH:23]=[C:22]([F:24])[C:21]([F:25])=[C:20]([F:26])[CH:19]=4)=[N:12]3)[CH:8]=[CH:9][C:2]=12>C1COCC1.[Ni]>[NH2:4][C:3]1[CH:6]=[C:7]([CH:8]=[CH:9][C:2]=1[NH2:1])[CH2:10][N:11]1[C:16](=[O:17])[CH:15]=[CH:14][C:13]([C:18]2[CH:19]=[C:20]([F:26])[C:21]([F:25])=[C:22]([F:24])[CH:23]=2)=[N:12]1

Participants

4

Reactant 1

HCID 594068142-Benzo-1,2,5-thiadiazol-5-ylmethyl-6-(3,4,5-trifluorophenyl)-2H-pyridazin-3-one

Product 1

HCID 594068152-(3,4-Diaminobenzyl)-6-(3,4,5-trifluorophenyl)-2H-pyridazin-3-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

3.5 g (9.4 mmol) of 2-benzo-1,2,5-thiadiazol-5-ylmethyl-6-(3,4,5-tri-fluorophenyl)-2H-pyridazin-3-one are dissolved in 35 ml of THF and hydrogenated under a hydrogen atmosphere in an autoclave at 30° C. under a pressure of 2 bar with 2 g of Raney Ni (70%, water-moist). After 17 h, a further 3 g of Raney Ni (70%, water-moist) are added, and the mixture is hydrogenated at 35° C. under a pressure of 2 bar for a further 16 h. The catalyst is separated off, rinsed, and the filtrate is evaporated to dryness.

Workup

  1. waitthe mixture is hydrogenated at 35° C. under a pressure of 2 bar for a further 16 h
  2. customThe catalyst is separated off
  3. washrinsed
  4. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-efd99de586954a9d9ba326a64be923e1
Source dataset
uspto-grants-2013_05
Patent number
US08445489B2

Reaction notes

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