P-Toluenesulfonamide → HCID 178427615, compound

HRID 2302016Notes

Reaction equation

HRID 2302016 reaction equation
Cl.[NH:2]([CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:19]=[C:18]2[C:13]([CH2:14][CH:15]([CH2:21][C:22]([OH:24])=O)[C:16](=[O:20])[NH:17]2)=[CH:12][CH:11]=1)[C:3]([NH2:5])=[NH:4].[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31]([NH2:34])(=[O:33])=[O:32])=[CH:27][CH:26]=1.Cl.CN(C)CCCN=C=NCC.CN(C1C=CC=CN=1)C>CN(C=O)C>[CH3:35][C:25]1[CH:26]=[CH:27][C:28]([S:31]([NH:34][C:22](=[O:24])[CH2:21][CH:15]2[CH2:14][C:13]3[C:18](=[CH:19][C:10]([O:9][CH2:8][CH2:7][CH2:6][NH:2][C:3]([NH2:5])=[NH:4])=[CH:11][CH:12]=3)[NH:17][C:16]2=[O:20])(=[O:33])=[O:32])=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 6269P-ToluenesulfonamideHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178479466HCID 178479466, compound

Product 1

HCID 178427615HCID 178427615, compoundYield 6.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To [7-(3-guanidino-propoxy)-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl]-acetic acid hydrochloride (0.90 g) was added para-toluenesulfonamide (0.65 g), 1-[3-(dimethylamino)-propyl]-3-ethylcarbodiimide hydrochloride (0.73 g), dimethylaminopyridine (0.05 g), and DMF (40 mL) and the resulting slurry formed a solution as it was stirred under N2 at room temperature for 21 days. The DMF was removed by vacuum distillation. The golden oil was triturated with CH2Cl2 (25 mL) followed by EtOAc (25 mL). The resulting oil was dissolved in 10 mL of 25% CH3CN/H2O and chromatographed on a C18 reverse phase column, eluting with a gradient of 10% CH3CN/H2O to 40% CH3CN/H2O to afford the title compound (73 mg) as an ivory solid after lyophilization.

Workup

  1. customthe resulting slurry formed a solution as it
  2. customThe DMF was removed by vacuum distillation
  3. customThe golden oil was triturated with CH2Cl2 (25 mL)
  4. dissolutionThe resulting oil was dissolved in 10 mL of 25% CH3CN/H2O
  5. customchromatographed on a C18 reverse phase column
  6. washeluting with a gradient of 10% CH3CN/H2O to 40% CH3CN/H2O

Sources & evidence

ORD record
ord-1c93ee245e914d5dad4ea5988aac16fe
Source dataset
uspto-grants-2002_08
Patent number
US06429214B1

Reaction notes

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