Cyanogen Bromide → 7-(3,5-dimethylisoxazol-4-yl)-8-methoxy-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-imidazo[4,5-c]quinolin-2-amine

HRID 81996Notes

Reaction equation

HRID 81996 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([NH:18][CH2:19][CH:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[C:12]([NH2:17])[CH:13]=[N:14]3)=[CH:9][C:8]=2[O:26][CH3:27])=[C:5]([CH3:28])[O:4][N:3]=1.[N:29]#[C:30]Br>C(O)C>[CH3:1][C:2]1[C:6]([C:7]2[C:8]([O:26][CH3:27])=[CH:9][C:10]3[C:11]4[N:18]([CH2:19][CH:20]5[CH2:21][CH2:22][O:23][CH2:24][CH2:25]5)[C:30]([NH2:29])=[N:17][C:12]=4[CH:13]=[N:14][C:15]=3[CH:16]=2)=[C:5]([CH3:28])[O:4][N:3]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 709811557-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N4-((tetrahydro-2H-pyran-4-yl)methyl)quinoline-3,4-diamine

Product 1

HCID 665712817-(3,5-dimethylisoxazol-4-yl)-8-methoxy-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-imidazo[4,5-c]quinolin-2-amineYield 13.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7-(3,5-Dimethylisoxazol-4-yl)-6-methoxy-N4-((tetrahydro-2H-pyran-4-yl)methyl)quinoline-3,4-diamine (for a preparation see Intermediate 17) (32 mg, 0.084 mmol) was dissolved in ethanol (3 ml) and cyanogen bromide (8.86 mg, 0.084 mmol) was added, then the mixture stirred overnight at room temperature. The reaction mixture was evaporated to dryness, the residue dissolved in DMSO (1 ml) and purified by MDAP (formate) to give 7-(3,5-dimethylisoxazol-4-yl)-8-methoxy-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-imidazo[4,5-c]quinolin-2-amine (4.5 mg, 0.011 mmol, 13.2% yield) as a yellow glass. LCMS (formate) Rt 0.65 min, MH+ 408

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionthe residue dissolved in DMSO (1 ml)
  3. custompurified by MDAP (formate)

Sources & evidence

ORD record
ord-2daaaa4cb4be4beea520ea6465de0e36
Source dataset
uspto-grants-2014_09
Patent number
US08846709B2

Reaction notes

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