1-Methylpiperazine → (11S)-11-[(4-Methylpiperazin-1-yl)methyl]-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-6-amine

HRID 549147Notes

Reaction equation

HRID 549147 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl[CH2:9][C@@H:10]1[N:15]2[C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=[C:18]([NH2:26])[C:17]=3[N:27]=[C:14]2[CH2:13][O:12][CH2:11]1>>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:9][C@@H:10]2[N:15]3[C:16]4[C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=[C:18]([NH2:26])[C:17]=4[N:27]=[C:14]3[CH2:13][O:12][CH2:11]2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 58406156(11R)-11-(chloromethyl)-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-6-amine

Product 1

HCID 58406175(11S)-11-[(4-Methylpiperazin-1-yl)methyl]-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-6-amineYield 16.5%

Conditions

Temperature
150 °C

Procedure

Methyl piperazine (0.3 mL, 2.5 mmol) was added to a vial containing (11R)-11-(chloromethyl)-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-6-amine (90 mg, 0.31 mmol). The vial was placed in a stainless-steel, high-pressure vessel and heated to 150° C. for 18 hours. The reaction mixture was cooled to ambient temperature. The resulting light brown oil was purified by chromatography (SiO2, 0-30% CMA/CHCl3). The resulting oil was slurried in acetonitrile to produce a solid which was isolated by filtration to give 18 mg of the desired product as a tan solid, mp 187-190° C.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customThe resulting light brown oil was purified by chromatography (SiO2, 0-30% CMA/CHCl3)
  3. customto produce a solid which
  4. customwas isolated by filtration

Sources & evidence

ORD record
ord-15917735a8474981ac71e78e978dd5d3
Source dataset
uspto-grants-2011_05
Patent number
US07943609B2

Reaction notes

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