Pyridine → HCID 131726133, compound

HRID 2100326Notes

Reaction equation

HRID 2100326 reaction equation
[CH3:1][N:2]1[CH2:7][CH:6]2[CH2:8][CH:3]1[CH2:4][N:5]2[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([NH2:19])=[CH:11][CH:10]=1.N1C=CC=CC=1.[CH3:26][C:27]1[CH:32]=[CH:31][C:30]([S:33]([Cl:36])(=[O:35])=[O:34])=[CH:29][CH:28]=1>C(Cl)Cl>[ClH:36].[CH3:26][C:27]1[CH:32]=[CH:31][C:30]([S:33]([NH:19][C:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:9]([N:5]3[CH2:4][CH:3]4[CH2:8][CH:6]3[CH2:7][N:2]4[CH3:1])=[CH:10][CH:11]=2)(=[O:35])=[O:34])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 21864824HCID 21864824, compound

Product 1

HCID 131726133HCID 131726133, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(5-methyl-2,5-diazabicyclo[2,2,1]hept-2-yl)-1-naphthylamine (0.210 g, 0.829 mmol) (prepared according to methods A and B), pyridine (468 μL, 5.80 mmol) in CH2Cl2 (3.0 mL) was added 4-methylbenzenesulfonyl chloride (0.158 g, 0.829 mmol) in CH2Cl2 (1.0 mL). The solution was stirred at room temperature for 16 hours and then concentrated. The crude product was purified via column chromatography (SiO2, CHCl3→CHCl3/MeOH/NH3 9:1:0.4%) to give the pure base which was converted to its HCl-salt: yield 160 mg (43%); 1H NMR (DMSO-d6) δ 10.78 (br s, 1H), 9.90-9.88 (m, 1H), 8.02-7.98 (m, 2H), 7.58-7.55 (m, 2H), 7.49-7.41 (m, 2H), 7.33-7.30 (m, 2H), 7.06-7.03 (m, 1H), 6.93-6.90 (m, 1H), 4.38-4.30 (m, 3H), 3.65-3.60 (m, 3H), 2.90-2.87 (m, 1H), 2.86-2.83 (m, 3H), 2.36 (br s, 2H), 2.35 (s, 3H); MS (posES-FIA) m/z=407.1655 (M+H) (calc 407.1667).

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified via column chromatography (SiO2, CHCl3→CHCl3/MeOH/NH3 9:1:0.4%)
  3. customto give the pure base which

Sources & evidence

ORD record
ord-adb0d988ca9245e08dca34e901cc7f28
Source dataset
uspto-grants-2009_08
Patent number
US07572787B2

Reaction notes

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