2-Bromoethyl methyl ether → HCID 117667193, compound

HRID 1526241Notes

Reaction equation

HRID 1526241 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([NH:13][C:14]2[CH:15]=[N:16][N:17]([CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[CH:18]=2)[C:5]([C:10]([NH2:12])=[O:11])=[N:6][C:7]=1[CH2:8][CH3:9].C(N(C(C)C)CC)(C)C.Br[CH2:35][CH2:36][O:37][CH3:38]>CN(C)C=O>[Cl:1][C:2]1[N:3]=[C:4]([NH:13][C:14]2[CH:15]=[N:16][N:17]([CH:19]3[CH2:24][CH2:23][N:22]([CH2:35][CH2:36][O:37][CH3:38])[CH2:21][CH2:20]3)[CH:18]=2)[C:5]([C:10]([NH2:12])=[O:11])=[N:6][C:7]=1[CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 809722-Bromoethyl methyl etherHCID 81531DiisopropylethylamineHCID 117667074HCID 117667074, compound

Product 1

HCID 117667193HCID 117667193, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-chloro-6-ethyl-3-{[1-(piperidin-4-yl)-1H-pyrazol-4-yl]amino}pyrazine-2-carboxamide (350 mg), diisopropylethylamine (685 μL), and N,N-dimethylformamide (3.5 mL) was added 2-bromoethylmethyl ether (282 μL), followed by reacting at 60° C. for 2 hours. The mixture was subjected to liquid separation by the addition of ethyl acetate and a saturated aqueous sodium hydrogen carbonate solution. The organic phase was washed with saturated brine and dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=99:1-90:10) to obtain 5-chloro-6-ethyl-3-({1-[1-(2-methoxyethyl)piperidin-4-yl]-1H-pyrazol-4-yl}amino)pyrazine-2-carboxamide (225 mg) as a yellow solid.

Workup

  1. customThe mixture was subjected to liquid separation by the addition of ethyl acetate
  2. washThe organic phase was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=99:1-90:10)

Sources & evidence

ORD record
ord-ff910a9bf2784c6597993e8a2494c020
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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