3-Fluoroaniline → N-(tert-butyl)-5-(4-((3-fluorophenyl)amino)-5-phenylphthalazin-1-yl)pyridine-3-sulfonamide

HRID 593719Notes

Reaction equation

HRID 593719 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:10]=[N:11][CH:12]=[C:13]([C:15]2[C:24]3[C:19](=[C:20]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:21]=[CH:22][CH:23]=3)[C:18](Cl)=[N:17][N:16]=2)[CH:14]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:32][C:33]1[CH:34]=[C:35]([CH:37]=[CH:38][CH:39]=1)[NH2:36]>>[C:1]([NH:5][S:6]([C:9]1[CH:10]=[N:11][CH:12]=[C:13]([C:15]2[C:24]3[C:19](=[C:20]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:21]=[CH:22][CH:23]=3)[C:18]([NH:36][C:35]3[CH:37]=[CH:38][CH:39]=[C:33]([F:32])[CH:34]=3)=[N:17][N:16]=2)[CH:14]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 97423-FluoroanilineHCID 90424399N-(tert-butyl)-5-(4-chloro-5-phenylphthalazin-1-yl)pyridine-3-sulfonamide

Product 1

HCID 90424675N-(tert-butyl)-5-(4-((3-fluorophenyl)amino)-5-phenylphthalazin-1-yl)pyridine-3-sulfonamideYield 60%

Procedure

N-(tert-Butyl)-5-(4-chloro-5-phenylphthalazin-1-yl)pyridine-3-sulfonamide (1.00 g, 2.21 mmol) in 3-fluoroaniline (2.94 g, 26.5 mmol) was heated in a sealed tube at 100° C. for 12 h. On cooling, the volatile components were removed under reduced pressure and the resulting residue was purified by combiflash (REDISEP®, silica gel, 24 g, 60% EtOAc/hexanes) to obtain N-(tert-butyl)-5-(4-((3-fluorophenyl)amino)-5-phenylphthalazin-1-yl)pyridine-3-sulfonamide (0.70 g, 60%) as a brown solid. LCMS (Condition 11): retention time 1.20 min, [M+1]=528.4. 1H NMR (400 MHz, DMSO-d6) δ 1.94 (s, 9 H), 6.50 (dd, J=1.2 Hz, J=8.4 Hz, 1 H), 6.76 (td, J=2.5 Hz, J=8.4 Hz, 1 H), 7.19-7.25 (m, 2 H), 7.53-7.66 (m, 6 H), 7.88-7.93 (m, 3 H), 8.05 (dd, J=6.8 Hz, J=8.4 Hz, 1 H), 8.54 (t, J=2.0 Hz, 1 H), 9.15 (d, J=2.0 Hz, 1 H), 9.16 (d, J=2.0 Hz, 1 H).

Workup

  1. temperatureOn cooling
  2. customthe volatile components were removed under reduced pressure
  3. customthe resulting residue was purified by combiflash (REDISEP®, silica gel, 24 g, 60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-478bb1b720a14e5f97fe1fe44224f8fa
Source dataset
uspto-grants-2016_01
Patent number
US09242966B2

Reaction notes

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