Pyridine → HCID 131726133, compound

HRID 856920Notes

Reaction equation

HRID 856920 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-naphtylamine (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-aa05435b62224c3190c9ce6fb12e234c
Source dataset
uspto-grants-2006_12
Patent number
US07144883B2

Reaction notes

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