Water → HCID 67434799, compound

HRID 1803390Notes

Reaction equation

HRID 1803390 reaction equation
[CH3:1][S:2]([N:5]1[CH2:22][C@H:21]([CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[N:8]2[C:9]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N+:12]([O-])=[CH:11][C:10]=3[N:20]=[C:7]2[CH2:6]1)(=[O:4])=[O:3].[NH4+:34].[OH-].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.O>C(Cl)Cl>[NH2:34][C:11]1[C:10]2[N:20]=[C:7]3[CH2:6][N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:22][C@H:21]([CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[N:8]3[C:9]=2[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 67435258HCID 67435258, compound

Product 1

HCID 67434799HCID 67434799, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl 3-[(11S)-9-(methylsulfonyl)-5-oxido-8,9,10,11-tetrahydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinolin-11-yl]propylcarbamate (6.37 g, 13.4 mmol) was dissolved in 120 mL of CH2Cl2 and treated with 12 mL of concentrated NH4OH solution. The mixture was stirred rapidly and then p-toluenesulfonyl chloride (2.81 g, 14.7 mmol) was carefully added. Rapid stirring was continued for 3 hours. The reaction mixture was treated with 100 mL of CH2Cl2 and 25 mL of H2O. The layers were separated and the organic portion was washed successively with 2% Na2CO3 solution (3×50 mL), H2O and brine. The organic portion was dried over Na2SO4, filtered and concentrated under reduced pressure. Chromatography (SiO2, 33% CMA/CHCl3) gave tert-butyl 3-[(11S)-6-amino-9-(methylsulfonyl)-8,9,10,11-tetrahydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinolin-11-yl]propylcarbamate (5.41 g) as light-orange foam.

Workup

  1. stirringRapid stirring
  2. customThe layers were separated
  3. washthe organic portion was washed successively with 2% Na2CO3 solution (3×50 mL), H2O and brine
  4. dry with materialThe organic portion was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cb3a043b23ba4dabb6affcc494eef6c6
Source dataset
uspto-grants-2013_01
Patent number
US08350034B2

Reaction notes

Loading…