Potassium Carbonate → N-{3-[3-(4-Cyanoanilino)propyl]-3-azabicyclo[3.2.1]oct-8-yl)-N-methyl-1-butanesulfonamide

HRID 411559Notes

Reaction equation

HRID 411559 reaction equation
[CH2:1]([S:5](Cl)(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].[CH3:9][NH:10][CH:11]1[CH:16]2[CH2:17][CH2:18][CH:12]1[CH2:13][N:14]([CH2:19][CH2:20][CH2:21][NH:22][C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=1)[CH2:15]2.C([O-])([O-])=O.[K+].[K+]>CC#N.C(Cl)(Cl)Cl>[C:27]([C:26]1[CH:25]=[CH:24][C:23]([NH:22][CH2:21][CH2:20][CH2:19][N:14]2[CH2:15][CH:16]3[CH:11]([N:10]([CH3:9])[S:5]([CH2:1][CH2:2][CH2:3][CH3:4])(=[O:7])=[O:6])[CH:12]([CH2:18][CH2:17]3)[CH2:13]2)=[CH:30][CH:29]=1)#[N:28]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 754301-Butanesulfonyl chlorideHCID 185408864-({3-[8-(Methylamino)-3-azabicyclo[3.2.1]oct-3-yl]propyl}amino)benzonitrile

Product 1

HCID 18541009N-{3-[3-(4-Cyanoanilino)propyl]-3-azabicyclo[3.2.1]oct-8-yl)-N-methyl-1-butanesulfonamideYield 35%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 1-butanesulfonyl chloride (39.1 mg, 0.25 mmol) in MeCN (2 mL) was added to a solution of 4-({3-[8-(methylamino)-3-azabicyclo[3.2.1]oct-3-yl]propyl}amino)benzonitrile (Preparation G; 74.6 mg, 0.25 mmol) in CHCl3 (0.5 mL). K2CO3 was added and the mixture was stirred at rt for 24 h. The mixture was filtered through a silica plug (500 mg), which plug was then eluted with MeCN:CHCl3 (80:20; 3×2.5 mL), followed by CHCl3:MeOH (95:5), to give the title compound in 35% yield.

Workup

  1. filtrationThe mixture was filtered through a silica plug (500 mg), which plug
  2. washwas then eluted with MeCN:CHCl3 (80:20; 3×2.5 mL)

Sources & evidence

ORD record
ord-2ccfe2348b2a4090aa8b01f471f3d953
Source dataset
uspto-grants-2003_05
Patent number
US06559162B2

Reaction notes

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