2-Bromoethyl methyl ether → HCID 68710203, compound

HRID 1809659Notes

Reaction equation

HRID 1809659 reaction equation
[CH2:1]([C:3]1[C:8]([O:9][C:10]2[C:11]([NH:23][C:24]3[S:28][N:27]=[C:26]([CH:29]4[CH2:35][CH:34]5[N:36]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH:31]([CH2:32][CH2:33]5)[CH2:30]4)[N:25]=3)=[N:12][CH:13]=[C:14]([S:16]CCC(OC)=O)[CH:15]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2].CC([O-])(C)C.[K+].Br[CH2:51][CH2:52][O:53][CH3:54]>C1COCC1>[CH2:1]([C:3]1[C:8]([O:9][C:10]2[C:11]([NH:23][C:24]3[S:28][N:27]=[C:26]([CH:29]4[CH2:30][CH:31]5[N:36]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH:34]([CH2:33][CH2:32]5)[CH2:35]4)[N:25]=3)=[N:12][CH:13]=[C:14]([S:16][CH2:51][CH2:52][O:53][CH3:54])[CH:15]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 809722-Bromoethyl methyl etherHCID 23665647Potassium tert-butoxideHCID 68708378HCID 68708378, compound

Product 1

HCID 68710203HCID 68710203, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 3-(5-(3-(2-ethylpyridin-3-yloxy)-5-(3-methoxy-3-oxopropylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)-8-azabicyclo[3.2.1]octane-8-carboxylate (115 mg, 0.183 mmol) was dissolved in THF (4 mL) and nitrogen was bubbled through the solution for 3 minutes. Potassium 2-methylpropan-2-olate (51.5 mg, 0.459 mmol) was added and the reaction was stirred at ambient temperature for 30 seconds. 1-Bromo-2-methoxyethane (19.0 μL, 0.202 mmol) was added and the reaction was stirred at ambient temperature for 30 minutes. The reaction was partitioned between EtOAc and aqueous NH4Cl. The organic layer was dried over sodium sulfate, filtered, concentrated and purified on silica gel (80% EtOAc in hexanes) to afford tert-butyl 3-(5-(3-(2-ethylpyridin-3-yloxy)-5-(2-methoxyethylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)-8-azabicyclo[3.2.1]octane-8-carboxylate (101 mg, 0.169 mmol, 91.9% yield).

Workup

  1. customnitrogen was bubbled through the solution for 3 minutes
  2. stirringthe reaction was stirred at ambient temperature for 30 minutes
  3. customThe reaction was partitioned between EtOAc and aqueous NH4Cl
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified on silica gel (80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d94ef39823944b0a991453893642bf16
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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