Water → HCID 11709986, compound

HRID 1803374Notes

Reaction equation

HRID 1803374 reaction equation
[NH2:1][CH2:2][C@@H:3]1[N:8]2[C:9]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]=[C:11]([NH2:19])[C:10]=3[N:20]=[C:7]2[CH2:6][O:5][CH2:4]1.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30].O>C(Cl)Cl>[NH2:19][C:11]1[C:10]2[N:20]=[C:7]3[CH2:6][O:5][CH2:4][C@H:3]([CH2:2][NH:1][S:29]([CH3:28])(=[O:31])=[O: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 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67435312HCID 67435312, compound

Product 1

HCID 11709986HCID 11709986, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(11S)-11-(Aminomethyl)-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-6-amine (778 mg, 2.89 mmol) was dissolved in 60 mL of CH2Cl2 and treated with triethylamine (804 μL, 5.78 mmol). The solution was cooled to 0° C. under N2. Methanesulfonyl chloride (224 μL, 2.89 mmol) was then added dropwise. After 75 minutes, the reaction was treated with H2O and extracted repeatedly with 10% methanol/CHCl3. The combined organic layers were washed successively with H2O and brine. The organic portion was dried over Na2SO4, filtered and concentrated under reduced pressure. Chromatography (SiO2, 10-15% methanol/CHCl3) gave an off-white solid. Crystallization from methanol gave N-{[(11S)-6-amino-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-11-yl]methyl}methanesulfonamide (487 mg) as white, powdery crystals, mp 285-288° C.

Workup

  1. extractionextracted repeatedly with 10% methanol/CHCl3
  2. washThe combined organic layers were washed successively with H2O and brine
  3. dry with materialThe organic portion was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customChromatography (SiO2, 10-15% methanol/CHCl3) gave an off-white solid
  7. customCrystallization from methanol

Sources & evidence

ORD record
ord-65187ba7e0764b7797f08382dbcb8bfd
Source dataset
uspto-grants-2013_01
Patent number
US08350034B2

Reaction notes

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