2-Bromoethyl methyl ether → HCID 57465599, compound

HRID 1043012Notes

Reaction equation

HRID 1043012 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[C:8]([O:29][CH3:30])=[CH:9][C:10]3[C:11]4[N:19]([C@@H:20]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=5)[CH3:21])[C:18](=[O:28])[NH:17][C:12]=4[CH:13]=[N:14][C:15]=3[CH:16]=2)=[C:5]([CH3:31])[O:4][N:3]=1.C(N=P1(N(CC)CC)N(C)CCCN1C)(C)(C)C.[CH3:50][O:51][CH2:52][CH2:53]Br>CN(C=O)C.CS(C)=O>[CH3:1][C:2]1[C:6]([C:7]2[C:8]([O:29][CH3:30])=[CH:9][C:10]3[C:11]4[N:19]([C@@H:20]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=5)[CH3:21])[C:18](=[O:28])[N:17]([CH2:53][CH2:52][O:51][CH3:50])[C:12]=4[CH:13]=[N:14][C:15]=3[CH:16]=2)=[C:5]([CH3:31])[O:4][N:3]=1

Participants

6

Reactant 3

HCID 809722-Bromoethyl methyl etherHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 529121897-(3,5-Dimethyl-1,2-oxazol-4-yl)-8-methoxy-1-[(1R)-1-(pyridin-2-yl)ethyl]-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one

Product 1

HCID 57465599HCID 57465599, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent2×

Procedure

7-(3,5-Dimethyl-4-isoxazolyl)-8-(methyloxy)-1-[(1R)-1-(2-pyridinyl)ethyl]-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one (for a preparation see Example 36, 100 mg) in DMF (5 ml) was treated with 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine, polymer bound (300 mg) and a solution of 2-bromoethyl methyl ether (40 mg) in DMF (0.5 ml). The reaction was stirred at ambient temperature, air atm for ˜3 h and then left at ambient temperature overnight. The reaction was filtered and the resin washed with methanol. The solvents were evaporated under a stream of nitrogen to leave a yellow gum which was dissolved in DMSO (1 ml) and purified by MDAP (Method formate). The product fractions were combined and reduced to dryness in vacuo to give 7-(3,5-dimethyl-4-isoxazolyl)-8-(methyloxy)-3-[2-(methyloxy)ethyl]-1-[(1R)-1-(2-pyridinyl)ethyl]-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one as a pale yellow gum (56 mg)

Workup

  1. waitleft at ambient temperature overnight
  2. filtrationThe reaction was filtered
  3. washthe resin washed with methanol
  4. customThe solvents were evaporated under a stream of nitrogen
  5. customto leave a yellow gum which
  6. custompurified by MDAP (Method formate)

Sources & evidence

ORD record
ord-4920d0a23f32410ea06b5ad248f99ba1
Source dataset
uspto-grants-2013_10
Patent number
US08557984B2

Reaction notes

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