Water → (11S)-11-Methyl-2-(prop-2-ynyloxy)-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-6-amine

HRID 221611Notes

Reaction equation

HRID 221611 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]3[CH2:18][O:17][CH2:16][C@H:15]([CH3:19])[N:14]3[C:10]=2[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:20])[CH:8]=2)[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:27](Br)[C:28]#[CH:29].O>CN(C=O)C>[CH3:19][C@@H:15]1[N:14]2[C:10]3[C:9]4[C:4](=[CH:5][CH:6]=[C:7]([O:20][CH2:29][C:28]#[CH:27])[CH:8]=4)[N:3]=[C:2]([NH2:1])[C:11]=3[N:12]=[C:13]2[CH2:18][O:17][CH2:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 10796Cesium carbonateHCID 58406167(11S)-6-amino-11-methyl-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-2-ol

Product 1

HCID 58406170(11S)-11-Methyl-2-(prop-2-ynyloxy)-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-6-amineYield 44.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (11S)-6-amino-11-methyl-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-2-ol (100 mg, 0.370 mmol) dissolved in 15 mL of DMF was treated with cesium carbonate (241 mg, 0.740 mmol) and propargyl bromide (49 mg, 0.410 mmol) and stirred overnight at ambient temperature. The dark brown mixture was then poured into 150 mL of H2O and stirred for 30 minutes. The mixture was filtered to give a dark brown solid. Chromatography (SiO2, 0-30% CMA/CHCl3) followed by crystallization from ethyl acetate gave 51 mg of the title compound as an off-white solid, mp 184-186° C.

Workup

  1. stirringstirred for 30 minutes
  2. filtrationThe mixture was filtered
  3. customto give a dark brown solid
  4. customChromatography (SiO2, 0-30% CMA/CHCl3) followed by crystallization from ethyl acetate

Sources & evidence

ORD record
ord-0fcce50839d4485c92ad917f4080c12d
Source dataset
uspto-grants-2012_06
Patent number
US08207162B2

Reaction notes

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