Water → (11S)-11-{[(4-fluorobenzyl)oxy]methyl}-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-6-amine

HRID 1035562Notes

Reaction equation

HRID 1035562 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][O:7][CH2:8][C@@H:9]2[N:14]3[C:15]4[C:24]5[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=5)[N+:18]([O-])=[CH:17][C:16]=4[N:26]=[C:13]3[CH2:12][O:11][CH2:10]2)=[CH:4][CH:3]=1.[NH4+:29].[OH-].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.O>C(Cl)Cl.C(Cl)(Cl)Cl>[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][O:7][CH2:8][C@@H:9]2[N:14]3[C:15]4[C:24]5[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=5)[N:18]=[C:17]([NH2:29])[C:16]=4[N:26]=[C:13]3[CH2:12][O:11][CH2:10]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 67156714(11S)-11-{[(4-Fluorobenzyl)oxy]methyl}-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinoline 5-oxide

Product 1

HCID 58406182(11S)-11-{[(4-fluorobenzyl)oxy]methyl}-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-6-amine

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

(11S)-11-{[(4-Fluorobenzyl)oxy]methyl}-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinoline 5-oxide (732 mg, 1.93 mmol) was dissolved in 50 mL of CH2Cl2 and treated with 5 mL of concentrated NH4OH solution. The mixture was stirred rapidly and then p-toluenesulfonyl chloride (370 mg, 1.93 mmol) was carefully added. Rapid stirring continued overnight. The reaction mixture was treated with 5 mL of H2O, and the layers were separated. The organic portion was washed with saturated NaHCO3 (2×50 mL) followed by brine (50 mL). The organic layer was then dried over Na2SO4, filtered, and concentrated under reduced pressure to give a crude orange solid. Chromatography (SiO2, 10-30% CMA/CHCl3) gave 236 mg of (11S)-11-{[(4-fluorobenzyl)oxy]methyl}-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-6-amine as a tan solid, mp 134-137° C.

Workup

  1. stirringRapid stirring continued overnight
  2. customthe layers were separated
  3. washThe organic portion was washed with saturated NaHCO3 (2×50 mL)
  4. dry with materialThe organic layer was then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a crude orange solid

Sources & evidence

ORD record
ord-ec76fc5bd2c247f3b7b9626a16dc38d0
Source dataset
uspto-grants-2013_10
Patent number
US08546383B2

Reaction notes

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