Water → HCID 66619826, compound

HRID 415549Notes

Reaction equation

HRID 415549 reaction equation
[CH3:1][C@@H:2]1[N:6]2[C:7]3[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[N+:10]([O-])=[CH:9][C:8]=3[N:18]=[C:5]2[N:4]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:3]1.[OH-].[NH4+:27].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.O>C(Cl)Cl.C(Cl)(Cl)Cl>[NH2:27][C:9]1[C:8]2[N:18]=[C:5]3[N:4]([C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[CH2:3][C@H:2]([CH3:1])[N:6]3[C:7]=2[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 66620473HCID 66620473, compound

Product 1

HCID 66619826HCID 66619826, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (10S)-10-methyl-9,10-dihydro-8H-imidazo[1′,2′:1,2]imidazo[4,5-c]quinoline-8-carboxylate 5-oxide (1.22 g, 3.58 mmol) in 50 mL of CH2Cl2 was treated with 5 mL of concentrated aqueous ammonium hydroxide and stirred vigorously. p-Toluenesulfonyl chloride (0.68 g, 3.58 mmol) was added in one portion and the reaction became slightly exothermic. The following day the reaction was treated with 5 mL of H2O, and the layers were separated. The organic layer was washed with saturated NaHCO3 solution (2×), then brine. It was dried over Na2SO4, filtered and concentrated to give a crude solid. Chromatography (SiO2, 0-20% CMA/CHCl3) afforded an off white solid, which was recrystallized from ethyl acetate to give tert-butyl (10S)-6-amino-10-methyl-9,10-dihydro-8H-imidazo[1′,2′:1,2]imidazo[4,5-c]quinoline-8-carboxylate (0.26 g) as a white solid.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with saturated NaHCO3 solution (2×)
  3. dry with materialIt was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude solid
  7. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a242bdc40f164830b92541b8f3976b06
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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