2-Pyridinemethanamine → N-(tert-butyl)-5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)pyridine-3-sulfonamide

HRID 593695Notes

Reaction equation

HRID 593695 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].[N:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH2:38][NH2:39]>C1(C)C=CC=CC=1>[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:39][CH2:38][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][N:32]=3)=[N:17][N:16]=2)[CH:14]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 195092-PyridinemethanamineHCID 90424399N-(tert-butyl)-5-(4-chloro-5-phenylphthalazin-1-yl)pyridine-3-sulfonamide

Product 1

HCID 90423975N-(tert-butyl)-5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)pyridine-3-sulfonamideYield 7.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-(tert-butyl)-5-(4-chloro-5-phenylphthalazin-1-yl)pyridine-3-sulfonamide (0.400 g, 0.883 mmol) in toluene (5 mL) was added pyridin-2-ylmethanamine (0.0950 g, 0.883 mmol) and the contents were heated at 100° C. for 12 h. The volatile components were removed under reduced pressure and the resulting residue was purified by preparative HPLC (Condition 16 as described in general methods) to yield N-(tert-butyl)-5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)pyridine-3-sulfonamide (35.0 mg, 7.55%) as a white solid. LCMS (Condition 4): retention time 2.47 min, [M+1]=525.2. HPLC (Condition 28): retention time=6.97 min, purity 96.32%. 1H NMR (400 MHz, CD3OD) δ 1.30 (s, 9 H), 4.68 (s, 2 H), 7.24 (dd, J=4.8 Hz, J=7.2 Hz, 1 H), 7.27 (d, J=7.6 Hz, 1 H), 7.52 (br s, 5 H), 7.72 (dd, J=1.6 Hz, J=7.6 Hz, 1 H), 7.77 (dd, J=1.2 Hz, J=7.2 Hz, 1 H), 7.84 (dd, J=1.2 Hz, J=8.4 Hz, 1 H), 7.91-7.96 (m, 1 H), 8.31 (d, J=4.4 Hz, 1 H), 8.55 (t, J=2.0 Hz, 1 H), 9.07 (d, J=2.0 Hz, 1 H), 9.18 (d, J=2.0 Hz, 1 H).

Workup

  1. customThe volatile components were removed under reduced pressure
  2. customthe resulting residue was purified by preparative HPLC (Condition 16 as described in general methods)

Sources & evidence

ORD record
ord-864dff59038947b1aca633541ecf5fdf
Source dataset
uspto-grants-2016_01
Patent number
US09242966B2

Reaction notes

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