Pyridine → HCID 9935206, compound

HRID 2118055Notes

Reaction equation

HRID 2118055 reaction equation
[CH3:1][N:2]([CH3:7])[S:3](Cl)(=[O:5])=[O:4].[Cl:8][C:9]1[CH:34]=[CH:33][C:12]2[N:13]3[C:17]([CH2:18][NH:19][CH2:20][C:11]=2[CH:10]=1)=[N:16][N:15]=[C:14]3[CH:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[CH2:23][CH2:22]1.N1C=CC=CC=1>ClCCl>[NH3:2].[CH3:1][N:2]([CH3:7])[S:3]([N:19]1[CH2:18][C:17]2[N:13]([C:14]([CH:21]3[CH2:26][CH2:25][N:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=4)[CH2:23][CH2:22]3)=[N:15][N:16]=2)[C:12]2[CH:33]=[CH:34][C:9]([Cl:8])=[CH:10][C:11]=2[CH2:20]1)(=[O:5])=[O:4]

Participants

6

Reactant 3

HCID 1049PyridineHCID 83372Dimethylsulphamoyl chloride2×HCID 113264888-Chloro-1-(3,4,5,6-tetrahydro-2h-[1,2']bipyridinyl-4-yl)-5,6-dihydro4h-2,3,5,10b-tetraaza-benzo[e]azulene

Product 2

HCID 222AmmoniaHCID 9935206HCID 9935206, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dimethylsulphamoyl chloride (0.12 ml, 1.08 mmol) was added to a solution of the amine from example 4 (140 mg, 0.36 mmol) and pyridine (90 μl, 1.08 mmol) in dichloromethane (8 ml), and the reaction mixture was stirred at room temperature for 18 hours. TLC analysis showed that starting material remained, so additional dimethylsulphamoyl chloride (0.08 ml, 0.72 mmol) was added and the mixture was stirred for a further 24 hours. The mixture was washed with saturated aqueous sodium bicarbonate solution, dried over magnesium sulphate, and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (95:5:0.5) as eluant, to afford the title compound as a pale yellow gum (120 mg).

Workup

  1. stirringthe mixture was stirred for a further 24 hours
  2. washThe mixture was washed with saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4a12b85f83f2403d82bd047273ef19c3
Source dataset
uspto-grants-2008_10
Patent number
US07442795B2

Reaction notes

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