Pyridine → HCID 131726126, compound

HRID 856915Notes

Reaction equation

HRID 856915 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([S:10]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([N:24]3[CH2:30][CH2:29][CH2:28][N:27]([CH3:31])[CH2:26][CH2:25]3)=[CH:16][CH:15]=2)(=[O:12])=[O:11])[CH:6]=[CH:7][C:8]=1F.N1C=CC=CC=1.FC1C=C(S([Cl:48])(=O)=O)C=CC=1>C(Cl)Cl>[ClH:48].[F:2][C:3]1[CH:4]=[C:5]([S:10]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([N:24]3[CH2:30][CH2:29][CH2:28][N:27]([CH3:31])[CH2:26][CH2:25]3)=[CH:16][CH:15]=2)(=[O:11])=[O:12])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 27342583-Fluorobenzenesulfonyl ChlorideHCID 131726127HCID 131726127, compound2×

Product 1

HCID 131726126HCID 131726126, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (intermediate 3 after reduction according to Method A) 4-(4-methyl-1,4-diazepan-1-yl)-1-naphthylamine (0.173 g, 0.676 mmol) and pyridine (450 μL, 4.73 mmol) in CH2Cl2 (3.0 mL) was added 3-fluorobenzenesulfonyl chloride (0.145 g, 0.743 mmol) in CH2Cl2 (1.0 mL). The solution was stirred at room temperature for 16 hours and the volatiles were evaporated. The crude product was purified by column chromatography (SiO2, CHCl3/MeOH/NH3 9:1:0.4%) to give 240 mg of the product as solid that was triturated with MeOH/ether to give 0.180 g (64%) of the free base which was converted to its HCl-salt: 1 H NMR (DMSO-d6) δ 11.07 (br s, 1H), 10.28 (br s, 1H), 8.20–8.16 (m, 1H), 7.98–7.94 (m, 1H), 7.60–7.40 (m, 6H), 7.16–7.12 (m, 1H), 7.06–7.02 (m, 1H), 3.65–3.30 (m, partly obscured by solvent signal, HDO, 6H), 3.26–3.18 (m, 2H), 2.84 (s, 3H), 2.30–2.05 (m, 2H); MS (posES-FIA) m/z=414 (M+H).

Workup

  1. customthe volatiles were evaporated
  2. customThe crude product was purified by column chromatography (SiO2, CHCl3/MeOH/NH3 9:1:0.4%)

Sources & evidence

ORD record
ord-9a8e3d92eaa74010b611b18158bdef02
Source dataset
uspto-grants-2006_12
Patent number
US07144883B2

Reaction notes

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