Pyridine → HCID 131726126, compound

HRID 2100321Notes

Reaction equation

HRID 2100321 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: 1H 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-aaa3eb0f24f248e29b57b9785c1eaeaf
Source dataset
uspto-grants-2009_08
Patent number
US07572787B2

Reaction notes

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